Water-soluble disazo dyestuffs

ABSTRACT

The novel water-soluble disazo dyestuffs consist of two monoazo dyestuff moieties each containing as diazo component an amine of the benzene or naphthalene series and as coupling component an amino-naphthol-mono- or disulfonic acid. The two moieties are bonded to each other via a bridge member bound to the amino groups of the coupling components and comprising two triazine radicals each containing a halogen atom, a sulfonic acid group or a thio ether or oxygen ether group or an amino group and the diazo components contain a fiber-reactive radical of the vinyl sulfone series. The metal-free dyestuffs can be transformed into the corresponding heavy metal complex dyestuffs, preferably copper, cobalt and chromium complex dyestuffs, by treatment with an agent donating a heavy metal cation. The novel dyestuffs are excellently suitable for dyeing and printing fiber material of natural and regenerated cellulose and natural, regenerated and synthetic polyamides. They are distinguished by a high tinctorial strength, a very good uptake from a long liquor, a good color- build up and good printing properties. The dyeings obtained therewith have a high fastness to processing and in use.

With the present invention, novel water-soluble dyestuffs of the generalformula (1) ##STR1## and their heavy metal complex compounds have beenfound.

The novel dyestuffs of the formula (1) can be in the form of the freeacid or in the form of their salts. They are preferably in the form ofthe salts, especially the alkali metal and alkaline earth metal saltsand in particular in the form of the sodium, potassium and calciumsalts. They are preferably used in the form of the alkali metal saltsfor dyeing and printing fiber materials.

In the above formula (1), the various radicals in the formula have thefollowing meaning: K₁ and K₂ are identical or different, preferablyidentical, and, described in the form of the free acid, represent aradical of the general formula ##STR2## in which R denotes a hydrogenatom or a lower alkyl group, such as a methyl group, and p denotes thenumber 1 or 2, preferably one of the radicals of the formulae ##STR3##the above radicals K₁ and K₂ in the formula being bonded via the aminogroups to the s-triazine radicals and in the ortho-position relative tothe hydroxy groups to the azo groups; D is a benzene nucleus ornaphthalene nucleus; R₁ is in the ortho-position relative to the azogroup and denotes a hydrogen atom, a halogen atom, preferably a chlorineor bromine atom, a lower alkyl group, preferably a methyl group, a loweralkoxy group, preferably a methoxy group, a hydroxy or carboxy group ora sulfonic acid group and R₂ is a hydrogen atom, a halogen atom,preferably a chlorine or bromine atom, a lower alkyl group, preferably amethyl group, a lower alkoxy group, preferably a methoxy group, a nitrogroup or a sulfonic acid group, it being possible for R₁ and R₂ to beidentical or different from one another; X represents theβ-thiosulfatoethyl or β-chloroethyl group, preferably the β-sulfatoethylor vinyl group; A is an aliphatic radical of 2-10 C atoms, especially analkylene radical of 2-6 C atoms, or an aliphatic radical, especially analkylene radical, of, in total, 2-6 C atoms, which can be interrupted byhetero-atoms and/or cycloaliphatic radicals, for example by 1 or 2 suchmembers from the group comprising --NH--, --O-- and --N(CH₃)-- and/or bya sulfur atom or a cyclohexylene group, or is a cycloaliphatic radical,such as, for example, a cyclohexylene radical, which can also besubstituted by 1-3 methyl groups, or is a benzene nucleus or anaphthalene nucleus, which can also be substituted by substituents fromthe group comprising lower alkyl, such as, for example, methyl or ethyl,lower alkoxy, such as, for example, methoxy and ethoxy, chlorine, sulfo,carboxy and lower alkanoylamino, such as acetylamino, or is one of theradicals of the formulae ##STR4## in which the benzene nuclei can besubstituted by substituents, preferably 1 or 2 substituents, from thegroup comprising lower alkyl, such as methyl, lower alkoxy, such asmethoxy, sulfo, carboxy and chlorine, and in which D₁ is a directcovalent bond or a bridge member, for example a bridge member of theformulae --CH₂ --, --CH₂ --CH₂ --, --O--CH₂ --CH₂ --O--, --CH═CH--,--NH--, --O--, --S--, --SO₂ --, --N═N--, --NH--CO--NH--, --CO--NH--,--NH--CO--, ##STR5## of a cyclohexylene radical, especially a radical ofthe formula ##STR6## preferably a bridge member of the formula --CH₂ --,--CH₂ --CH₂ --, --CH═CH--, --NH--, --SO₂ --, --CO--NH-- or --NH--CO-- orthe abovementioned bivalent radical of oxadiazole or preferably a directcovalent bond, and E represents a member of the formula --O--, --S--,--NH--, or --SO₂ --; and Y is a chlorine, fluorine or bromine atom or asulfonic acid group or a group which consists of a substituent bondedvia a sulfur or oxygen atom and is of the formula --S--R' or --O--R", inwhich R' is preferably a substituent from the group comprising loweralkyl, substituted lower alkyl, phenyl, naphthyl, substituted phenyl,substituted naphthyl or 2-benzthiazolyl, such as, for example, loweralkyl substituted by substituents from the group comprising hydroxy,lower alkoxy, sulfato, sulfo, carboxy, phenyl, naphthyl, substitutedphenyl and substituted naphthyl, or, for example, phenyl or naphthylsubstituted by substituents from the group comprising nitro, sulfo andcarboxy, and R" denotes a hydrogen atom or has the meaning of R' withthe exception of 2-benzthiazolyl, or Y is an amino group of the formula--NR₃ R₄, in which R₃ is a hydrogen atom, an optionally substitutedlower aliphatic radical or an optionally substituted araliphatic radicalor a cycloaliphatic radical, such as, for example, a lower alkyl radicalwhich can be substituted by one or two substituents from the groupcomprising hydroxy, sulfato, lower alkoxy, sulfo, carboxy and phenyl, oris a cyclohexyl radical, and R₄ represents a hydrogen atom, anoptionally substituted lower aliphatic radical, such as, for example, alower alkyl radical which can be substituted by hydroxy, lower alkoxy,sulfato, sulfo and carboxy, or represents an optionally substitutedaromatic radical, such as, for example, a phenyl or naphthyl radical,which can be substituted by one or two substituents from the groupcomprising hydroxy, carboxy, sulfo, lower alkyl and lower alkoxy, orrepresents an optionally substituted araliphatic radical, such as, forexample, a lower alkyl radical which can be substituted by phenyl ornaphthyl, or represents a hydroxy group or a lower alkoxy group orrepresents an optionally substituted amino group, such as, for example,the amino group or a phenylamino or lower alkylamino group, or in whichR₃ and R₄ together with the nitrogen atom form a ring containing a loweralkylene radical and optionally a hetero-atom, such as, for example, anitrogen atom or oxygen atom, such as, for example a morpholine,piperidine or piperazine ring.

The two radicals ##STR7## in the formula can be identical or differentin the general formula (1); preferably they are identical.

Here and in the text which follows, the term "lower" used in thedefinitions denotes that the alkyl or alkylene radical contained in thegroup consists of 1-4 C atoms.

The present invention also relates to heavy metal complex dyestuffs ofthe abovementioned formula (1), in which one or both of the R₁ srepresents a hydroxyl group and bond the metal as a complex with thehydroxy groups of the coupling component or components. The heavy metalcomplex dyestuffs are preferably those in which two heavy metalequivalents are each bonded in complex form to one molecule of theformula (1), specifically in each case to the hydroxy groups R₁ andthose of the aminonaphthol-disulfonic acid radicals. Preferred heavymetal complex dyestuffs are the copper, cobalt and chromium complexdyestuffs of the formula (1) according to the invention, especially thecopper complex dyestuffs.

The present invention also relates to a process for the manufacture ofthe novel dyestuffs of the formula (1), which comprises reacting 2 molesof the diazonium compound of one or two aromatic amines, preferably asingle aromatic amine of the general formula (2) ##STR8## in which D,R₁, R₂ and X are as defined above and R₁ is in the ortho-positionrelative to the amino group, with 1 mole of a coupling component of thegeneral formula (3) ##STR9## in which A, K₁, K₂ and Y are as definedabove.

The present invention also relates to a process for the manufacture ofthe heavy metal complex dyestuffs of the abovementioned general formula(1), which comprises reacting the metal-free dyestuffs of the formula(1) in which R₁ represents a hydrogen atom or a hydroxy or lower alkoxygroup, if desired immediately following the abovementioned procedure,according to the invention, for the manufacture of the metal-freedyestuffs of the formula (1), in a manner which is in itself known, ifappropriate in the presence of an oxidizing agent, with a metal donor.

The metal-free dyestuffs of the formula (1) or their heavy metalcomplexes can, however, also be manufactured in a manner according tothe invention by subjecting one mole of each of the monoazo compounds ofthe general formulae (4) and (5) ##STR10## described in the form of thefree acids, in which R₁, R₂, D and X are as defined above and K₃ and K₄are identical or different, preferably identical, and represent aradical of the general formula ##STR11## in which R and p are as definedabove, and preferably represent one of the radicals of the formulae##STR12## the azo group being bonded to the radicals K₃ and K₄ informulae 4 and 5 in each case in the ortho-position relative to thehydroxy group of the naphthol radical, or two moles of their heavy metalcomplex compounds in which R₁ is a hydroxy group, preferably the 1:1copper complex compounds, or 1 mole of the heavy metal complex compoundof the formula (4) or (5) and 1 mole of the metal-free compound of theformula (5) or, respectively, (4) to a condensation reaction with ahalogeno-s-triazine compound of the formula (6) ##STR13## in which A andY are as defined above and Hal represents a chlorine, bromine orfluorine atom, and, if desired, subsequently reacting the product in amanner which is in itself known, if appropriate in the presence of anoxidizing agent, with an agent which donates a heavy metal cation.

The novel metal-free or metal-containing dyestuffs of the formula (1) inwhich K₁ and K₂ are identical can also be manufactured in a manneraccording to the invention by subjecting 2 moles of a monoazo compoundof the formula (7) ##STR14## in which D, R₁, R₂, X, Y and Hal are asdefined above and K₁ represents one of the abovementioned radicals,which is identical to K₂, to a condensation reaction with one mole of acompound of the formula (8)

    H.sub.2 N--A--NH.sub.2                                     ( 8)

in which A is as defined above, and, if desired, reacting the metal-freedyestuff of the formula (1), thus obtained, in a manner which is initself known, if appropriate in the presence of an oxidizing agent, witha metal donor.

The abovementioned condensation reactions are preferably carried out inaqueous solution, optionally in the presence of organic solvents, atroom temperature (15°-25° C.) or elevated temperature (up to 120° C.) inaccordance with known processes in an analogous manner well known tothose skilled in the art. If the heavy metal complex dyestuffs accordingto the invention are manufactured by subsequent metallization, asindicated here, one or both of the R₁ s can be a hydrogen atom, ahydroxy group or a lower alkoxy group.

It is also possible, in a manner according to the invention, to converta heavy metal complex dyestuff according to formula (1) into a heavymetal dyestuff according to the invention which contains a differentheavy metal central atom, by splitting the original heavy metal atomfrom the complex dyestuff analogously to the known methods (see, forexample, Angew. Chem. 64, 397 (1952)) and reacting the resultingo,o'-dihydroxy-azo dyestuff with an agent which supplies the other heavymetal atom. Thus, for example, copper complex dyestuffs of the formula(1) can be converted to the corresponding chromium or cobalt complexdyestuffs of the formula (1).

Preferred dyestuffs, according to the invention, of the formula (1) andtheir heavy metal complexes are those in which D represents a benzenenucleus and also those in which D represents a naphthalene nucleus inwhich the azo group is bonded in the β-position of this naphthalenenucleus. Further preferred dyestuffs according to the invention arethose in which Y denotes a halogen atom, preferably a chlorine atom.Furthermore, dyestuffs of particular importance are those in which K₁and K₂, which can be identical or different, represent theabovementioned divalent radical of 1-amino-naphthol(8)-3,6-disulfonicacid, 1-aminonaphthol(8)-4,6-disulfonic acid,2-amino-naphthol(8)-6-sulfonic acid or 2-amino-naphthol(5)-7-sulfonicacid.

In addition to the said halogen atoms and the sulfonic acid group, thefollowing individual groups are to be singled out for the substituent Yin the triazine ring of the dyestuffs of the formula (1) or of thecompounds of the formulae (3), (6) and (7):

--O--CH₃, --O--C₂ H₅, --O--CH₂ --CH₂ --CH₃, --OH, ##STR15## --S--CH₂--CH₂ --OH, ##STR16## --S--CH₂ --COOH, ##STR17## --NH₂, --NH--CH₃,--NHC₂ H₅, --NHC₃ H₇, ##STR18## --NH--CH₂ --CH₂ --OH, --NH--CH₂ --CH₂--OSO₃ H, --NH--CH₂ --CH₂ --O--CH₃, ##STR19## --NH--CH₂ --CH₂ --SO₃ H,--NH--CH₂ --COOH, ##STR20## --NH--OH, --NH--NH₂, ##STR21##

Preferably, the radical Y in the formula denotes a chlorine, bromine orfluorine atom or a sulfo, amino, methylamino, dimethylamino,β-hydroxyethyl-amino, β-methoxyethyl-amino, β-sulfatoethyl-amino,β-sulfoethyl-amino, N-methyl-N-β-sulfoethyl-amino, carboxymethyl-amino,N-β-carboxyethyl-amino, N-(carboxyphenyl)-amino, N-(sulfophenyl)-amino,N-(disulfo-phenyl)-amino, N-(sulfonaphthyl(1))-amino, N-methylanilino,morpholino, iso-propoxy, phenoxy or β-hydroxyethylthioether group.

Further compounds of the formula (1) which should be mentioned as beingpreferred are those in which D is a benzene nucleus and R₁, R₂, A, K₁,K₂, Y and X have one of the abovementioned meanings, especially thepreferred meanings, and also compounds of the formula (1) in which Ddenotes a naphthalene nucleus which is bonded in the 2-position to theazo group, R₁ represents a hydrogen atom and R₂ represents the sulfogroup in the 6-position of the naphthalene nucleus, or R₁ denotes thesulfo group and R₂ is hydrogen, and K₁, K₂, A, Y and X have one of theabovementioned meanings, especially the preferred meanings.

Further preferred compounds of the formula (1) are those in which Drepresents a benzene nucleus, in which the group --SO₂ --X is in themeta-position or para-position relative to the azo group, or in which Ddenotes a naphthalene nucleus which is bonded in the 2-position to theazo group and which contains the group --SO₂ --X in the 6-position or8-position, and A, R₁, R₂, K₁, K₂, Y and X have one of theabovementioned meanings, especially the preferred meanings.

Further compounds to be singled out are those in which A represents aradical of the formula ##STR22##

Further preferred compounds of the formula (1) to be mentioned are thosein which D, R₁, R₂ and A have one of the abovementioned meanings,especially the preferred meanings, X represents the β-sulfatoethylradical and Y represents a chlorine atom and K₁ denotes a radical of theformula ##STR23## and K₂ denotes a radical of the formula ##STR24##Amongst these compounds, compounds in which D is a benzene nucleus, R₁and R₂ are each hydrogen, and the β-sulfatoethylsulfonyl group is in thep-position relative to the azo group, are particularly preferred.

The aromatic amines of the formula (2) are known, for example fromGerman Patent Specifications 1,278,041, 1,276,842, 1,150,163, 1,126,542and 1,153,029, from German Offenlegungsschriften 2,154,943, 2,100,080,2,049,664, 2,142,728, 2,034,591 and 1,943,904 or from GermanAuslegeschrift 1,204,666.

Aromatic amines of the formula (2) which may be mentioned are, inparticular, the following compounds: aniline-3-β-sulfatoethylsulfone,aniline-4-β-sulfatoethylsulfone,2-amino-toluene-4-β-sulfatoethylsulfone,2-amino-anisole-4-β-sulfatoethylsulfone,2-amino-anisole-5-β-sulfatoethylsulfone,2-amino-4-β-sulfatoethylsulfonyl-benzoic acid,2-methoxy-5-methyl-aniline-4-β-sulfatoethylsulfone,2,5-dimethoxy-aniline-4-β-sulfatoethylsulfone,2,4-dimethoxy-aniline-5-β-sulfatoethylsulfone,4-aminoanisole-2-β-sulfatoethylsulfone,4-aminotoluene-2-β-sulfatoethylsulfone,4-β-sulfatoethylsulfonyl-aniline-2-sulfonic acid,5-β-sulfatoethylsulfonyl-aniline-2-sulfonic acid,2-chloroaniline-4-β-sulfatoethylsulfone,2-chloroaniline-5-β-sulfatoethylsulfone,2-bromoaniline-4-β-sulfatoethylsulfone,2,6-dichloroaniline-4-β-sulfatoethylsulfone,2,6-dimethyl-aniline-4-β-sulfatoethylsulfone,2,6-dimethyl-aniline-3-β-sulfatoethylsulfone,2-amino-phenol-4-β-sulfatoethylsulfone,2-amino-phenol-5-β-sulfatoethylsulfone,6-bromo-2-amino-phenol-4-β-sulfatoethylsulfone,6-chloro-2-amino-phenol-4-β-sulfatoethylsulfone,6-nitro-2-amino-phenol-4-β-sulfatoethylsulfone,4-methyl-2-amino-phenol-5-β-sulfatoethylsulfone,2-naphthylamine-5-β-sulfatoethylsulfone,2-naphthylamine-8-β-sulfatoethylsulfone,8-β-sulfatoethylsulfonyl-2-amino-naphthalene-6-sulfonic acid,6-β-sulfatoethylsulfonyl-2-amino-naphthalene-1-sulfonic acid,2-naphthylamine-6-β-sulfatoethylsulfone and the correspondingvinylsulfonyl, β-thiosulfatoethylsulfonyl and β-chloroethylsulfonylcompounds.

The coupling components of the formula (3) can, for example, easily beprepared in a manner which is analogous to the procedures described inGerman Patent Specification 485,185 and which is well-known to thoseskilled in the art. Coupling components of the formula (3) which may bementioned are, in particular, the compounds of the formula (3) which arelisted in the following table and in which A and Y have one of theabovementioned meanings:

    ______________________________________                                        Coupling components of the formula (3):                                       HK.sub.1         K.sub.2H                                                     ______________________________________                                         ##STR25##                                                                                    ##STR26##                                                                     ##STR27##                                                      ##STR28##     "                                                              "                                                                                             ##STR29##                                                      ##STR30##                                                                                    ##STR31##                                                     "                                                                                             ##STR32##                                                      ##STR33##     "                                                              "                                                                                             ##STR34##                                                     "                                                                                             ##STR35##                                                     "                                                                                             ##STR36##                                                      ##STR37##     "                                                              "                                                                                             ##STR38##                                                     "                                                                                             ##STR39##                                                      ##STR40##     "                                                              "                                                                                             ##STR41##                                                      ##STR42##     "                                                              "                                                                                             ##STR43##                                                     "                                                                                             ##STR44##                                                      ##STR45##     "                                                              "                                                                                             ##STR46##                                                      ##STR47##                                                                                    ##STR48##                                                      ##STR49##     "                                                               ##STR50##     "                                                              "                                                                                             ##STR51##                                                      ##STR52##     "                                                               ##STR53##     "                                                               ##STR54##     "                                                              "                                                                                             ##STR55##                                                     "                                                                                             ##STR56##                                                      ##STR57##     "                                                               ##STR58##     "                                                               ##STR59##     "                                                               ##STR60##                                                                                    ##STR61##                                                      ##STR62##     "                                                               ##STR63##     "                                                              "                                                                                             ##STR64##                                                      ##STR65##     "                                                               ##STR66##     "                                                               ##STR67##                                                                                    ##STR68##                                                      ##STR69##     "                                                               ##STR70##     "                                                               ##STR71##     "                                                              "                                                                                             ##STR72##                                                      ##STR73##                                                                                    ##STR74##                                                      ##STR75##     "                                                              "                                                                                             ##STR76##                                                      ##STR77##     "                                                              "                                                                                             ##STR78##                                                      ##STR79##                                                                                    ##STR80##                                                      ##STR81##     "                                                               ##STR82##                                                                                    ##STR83##                                                     "                                                                                             ##STR84##                                                      ##STR85##     "                                                              "                                                                                             ##STR86##                                                     "                                                                                             ##STR87##                                                      ##STR88##     "                                                              "                                                                                             ##STR89##                                                      ##STR90##     "                                                              "                                                                                             ##STR91##                                                      ##STR92##     "                                                               ##STR93##                                                                                    ##STR94##                                                     "                                                                                             ##STR95##                                                      ##STR96##     "                                                              "                                                                                             ##STR97##                                                      ##STR98##     "                                                              "                                                                                             ##STR99##                                                     "                                                                                             ##STR100##                                                    ______________________________________                                    

The diazotization of the aromatic amines of the formula (2) is carriedout by generally known methods. However, care must be taken that thesearomatic amines, and the diazonium salts obtained therefrom, are notsubjected to strongly alkaline conditions during processing.

The coupling of the diazotized amines with the coupling components ofthe formula (3) is preferably carried out in a pH range between 3 and 7,at temperatures between -5° and +30° C.

If a hydroxy group is present in the o-position relative to the azobridges in the radicals of the diazo components, that is to say if R₁=OH, the dyestuffs are converted to the heavy metal complex dyestuffs byadding a heavy metal donor to the dyestuff solution or the dyestuffsuspension, if necessary with an acid-binding agent and if necessary bytreatment at elevated temperature (in general the reaction can becarried out at 0°-120° C.) until the conversion to the desired heavymetal complex dyestuff is complete.

Examples of heavy metal donors which can be used are: copper salts, suchas copper sulfate, copper chloride, copper acetate or copper carbonate,chromium salts, such as chromium formate, chromium acetate, chromiumsulfate, potash/chrome alum or chromium/salicylic acid, or cobalt salts,such as cobalt sulfate, cobalt chloride or a cobalt/tartaric acidcomplex.

Acid-binding agents used when converting the dyestuffs to the heavymetal complex dyestuffs are preferably alkali metal salts of weakinorganic or organic acids, such as sodium carbonate, sodium bicarbonateor sodium acetate.

If R₁ is an alkoxy group, preferably a methoxy group, this can beconverted by known methods, during the reaction to convert the dyestuffto the heavy metal complex dyestuff, preferably the copper complexdyestuff, to a hydroxy group and the latter can participate in theformation of the complex.

If R₁ is a hydrogen atom, this can be replaced by a hydroxy group underthe conditions of oxidative coppering [Angew. Chem. 70, 232-238 (1958)],with simultaneous incorporation of the said hydroxy group into thecomplex compound. The oxidizing agents used are advantageouslyderivatives of hydrogen peroxide, such as sodium peroxide, salts ofperoxysulfuric acid or salts of perboric acid, but preferably hydrogenperoxide itself. Advantageous reaction conditions in general lie at20°-100° C. and at pH values between 7 and 3.

The resulting dyestuffs of the formula (1) or their heavy metal complexcompounds are separated off by generally known methods, either byprecipitating from the reaction medium by means of electrolytes, suchas, for example, sodium chloride or potassium chloride, or byevaporating the reaction solution, for example by spray-drying. If thelatter method of isolating the dyestuff is chosen, it is advisable,before evaporating, to remove any amounts of sulfate which may bepresent in the solutions by precipitating these as gypsum and separatingthem off by filtration. In some cases, it can also be desirable tosupply the dyestuff solution direct, if appropriate after adding buffersubstances, as a liquid preparation for use in dyeing.

The present invention also relates to the dyeing and printing ofcellulose and polyamide fiber materials with the dyestuffs according tothe invention.

Cellulose fiber materials are understood as meaning preferably cottonand regenerated cellulose, but also other vegetable fibers, such aslinen, hemp and jute. Polyamide fibers are to be understood as meaningboth those of natural origin and those of synthetic origin, that is tosay both wool and other animal hairs and silk and also polyamide 6,6,polyamide 6, polyamide 11 or polyamide 4.

The dyestuffs according to the invention can be applied to the saidsubstrates by the application techniques known for reactive dyestuffs.

Thus, with these dyestuffs very good color yields are obtained oncellulose fibers by the exhaustion method from a long liquor, using verydiverse alkali additives.

Excellent color yields are also obtained on cellulose fibers by the padmethod, and the dyes can be fixed by a residence time at roomtemperature, by steaming or with dry heat.

Intense prints with outlines in a good state and a clear white groundare also obtained by the conventional printing processes for cellulosefibers--in a single phase in the presence of sodium bicarbonate or otheracid-binding agents in the printing paste with subsequent steaming at101°-103° C. or in two phases, printing with a neutral or weakly acidprinting paste and then either passing through a hotelectrolyte-containing alkaline bath or over-padding with an alkalineelectrolyte-containing padding liquor and then developing by means of aresidence time, steaming or dry heat. The appearance of the prints isonly slightly dependent on changing fixing conditions. Both in dyeingand in printing, the degrees of fixation obtained with the dyestuffsaccording to the invention are exceptionally high.

With regard to the coloristic properties of the dyestuffs according tothe invention, it must be emphasized in particular that these dyestuffsare distinguished by good stability in printing pastes and paddingliquors, including in the presence of alkali, by a very good uptake froma long liquor, by good color build-up by the conventional dyeing andprinting processes, by an identical depth of shade when dyeing on cottonand regenerated cellulose fibers, by levelness of the dyeings and printsproduced therewith and also by a uniform appearance of the dyeings froma long liquor on the addition of various amounts of electrolytes, suchas sodium sulfate or sodium chloride.

The fastness properties of the dyeings and prints obtained with the aidof the dyestuffs according to the invention, especially those oncellulose fibers, are appreciable. This equally applies in the case ofthe most important fastnesses to manufacturing processes and fastnessproperties in use. The fastness to light, the fastness to wetprocessing, such as fastness to washing, fastness to milling, fastnessto water and fastness to seawater, and the fastness to ironing andfastness to rubbing should be mentioned in particular.

The dyeings on polyamide fibers are usually carried out from an acidmedium. Thus, for example, acetic acid or acetic acid and ammoniumacetate can be added to the dyebath in order to obtain the desired pHvalue. In order to obtain a usable levelness of the dyeings, it isadvisable to add conventional levelling agents, for example those basedon a reaction product of cyanuric chloride with three times the molaramount of an aminobenzenesulfonic acid and/or of anaminonaphthalenesulfonic acid and/or those based on a reaction productof, for example, stearylamine with ethylene oxide. The dyeings can becarried out either at the boil or at 110° to 120° C.

The examples which follow serve to illustrate the invention. Therelationship between parts by weight and parts by volume is the same asthat between kilogram and liter. The percentages are by weight unlessstated otherwise.

EXAMPLE 1

(a) 18.5 parts by weight of cyanuric chloride are dissolved in 60 partsby volume of acetone and the solution is then allowed to run into 500parts by volume of cold water, with stirring. A solution of 31.9 partsby weight of 1-amino-8-naphthol-3,6-disulfonic acid in 150 parts byvolume of water, which has been neutralized with 12 parts by weight ofaqueous 33% sodium hydroxide solution, is added immediately to thesuspension thus obtained and the resulting mixture is stirred for 15minutes. A neutral solution of 20.7 parts by weight of the disodium saltof 4,4'-diaminostilbene-2,2'-disulfonic acid in 250 parts by volume ofwater is then added, immediately thereafter 30 parts by weight ofcrystalline sodium acetate are introduced and the mixture is thenstirred for several hours. The diazonium salt solution obtained in thefollowing way is then added to the reaction mixture thus obtained:

28.1 parts by weight of aniline-4-β-sulfatoethylsulfone are dissolved in140 parts by volume of water and 60 parts by weight of ice with theaddition of about 6.5 parts by weight of calcined sodium carbonate togive a neutral solution, 20.5 parts by volume of aqueous 5 N sodiumnitrite solution are then added and the solution thus obtained isallowed to run into a mixture of 25 parts by volume of aqueous 31%hydrochloric acid and 150 parts by weight of ice. The mixture is stirredfor 1 hour at 0°-5° C., excess nitrous acid is then destroyed with alittle amidosulfonic acid and the pH is then adjusted to 5.5-6.0 with 4parts by weight of sodium bicarbonate. The reaction mixture describedinitially is added to this diazonium salt solution and the couplingreaction is carried out at 10°-12° C. and pH 5.5-6.0 for 15 hours. Thecoupling mixture is then warmed to 60° C. and, after adding 5 parts byweight of kieselguhr, is clarified. The dyestuff is precipitated fromthe filtrate by introducing 25%-based on the volume--of sodium chlorideand is filtered off, dried in vacuo at 60° C. and ground.

This gives 253 parts by weight of a brown dyestuff powder, with whichred dyeings of good general fastness properties can be produced oncellulose materials in the presence of alkaline agents.

The dyestuff has the following constitution: ##STR101##

(b) The dyestuff with virtually the same properties can be obtained when2 moles of the dyestuff of the formula ##STR102## described in JapanesePublished Patent Sho 38-23,287, are reacted with one mole of4,4'-diaminostilbene-2,2'-disulfonic acid at a somewhat highertemperature and a pH of 6.5-7.0 in an aqueous medium.

(c) Furthermore, the dyestuff can be prepared when 2 moles of theaminoazo dyestuff of the formula ##STR103## which can be obtained bycoupling diazotized aniline-4-β-hydroxyethylsulfone with1-acetylamino-8-naphthol-3,6-disulfonic acid, saponifying theacetylamino group to the free amino group and esterifying theβ-hydroxyethylsulfonyl group by means of an excess of 100% strengthsulfuric acid to the β-sulfatoethylsulfonyl group, are reacted with 1mole of the compound of the formula ##STR104## which can be prepared ina known manner by reacting a solution of 1 mole of the disodium salt of4,4'-diaminostilbene-2,2'-disulfonic acid in approximately 15 times theamount by weight of water with a solution of 2 moles of cyanuricchloride in acetone at 0° C., with the addition of a solution of barely2 moles of sodium carbonate in 5 times the amount by weight of water, inan aqueous medium at elevated temperature, a pH value of 6.9-7.2 beingmaintained.

EXAMPLE 2

If a neutral solution of 22.4 parts by weight of the disodium salt of4,4'-diamino-3,3'-dimethoxy-diphenyl-6,6'-disulfonic acid in 300 partsby volume of water is employed in place of the solution of 20.7 parts byweight of the disodium salt of 4,4'-diaminostilbene-2,2'-disulfonic acidin Example 1 and in other respects the procedure is as described inExample 1, this gives, when the dyestuff is precipitated with 20%, basedon the volume, of potassium chloride, filtered off, dried in vacuo at60° C. and ground, 169 parts by weight of a brown powder with which reddyeings and prints of good general fastness properties can be producedon cellulose materials in the presence of acid-binding agents.

The dyestuff has the following constitution: ##STR105##

Dyestuffs can be obtained in a manner analogous to that described inExamples 1 and 2 from the diazo components and coupling componentslisted in the table which follows; these dyestuffs dye and print cottonin the indicated color shades.

                                      TABLE 1                                     __________________________________________________________________________    Example                                             Color shade               No.    Diazo component     Coupling component       on cotton                 __________________________________________________________________________    3      2 moles of aniline-3-β-                                                                      condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               4      2 moles of 2-aminoanisole-5-                                                                      condensation product of 2 moles of                                                                     claret                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               5      2 moles of 2-aminoanisole-4-                                                                      condensation product of 2 moles of                                                                     claret                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               6      2 moles of 2-aminotoluene-4-                                                                      condensation product of 2 moles of                                                                     red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               7      2 moles of 2-methoxy-5-methyl-                                                                    condensation product of 2 moles of                                                                     claret                           aniline-4-β-sulfatoethyl-                                                                    primary condensation product obtained                     sulfone             from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               8      2 moles of 2,5-dimethoxy-                                                                         condensation product of 2 moles of                                                                     claret                           aniline-4-β-sulfatoethylsulfone                                                              primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               9      2 moles of 2-chloroaniline-5-                                                                     condensation product of 2 moles of                                                                     red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               10     2 moles of 2,6-dimethylaniline-                                                                   condensation product of 2 moles of                                                                     red                              4-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               11     2 moles of 2,6-dimethylaniline-                                                                   condensation product of 2 moles of                                                                     red                              3-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               12     2 moles of 2,4-dimethoxyaniline-                                                                  condensation product of 2 moles of                                                                     bluish-tinged red                5-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               13     2 moles of 2-aminoanisole-4-β-                                                               condensation product of 2 moles of                                                                     claret                           thiosulfatoethylsulfone                                                                           primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               14     2 moles of aniline-4-β-                                                                      condensation product of 2 moles of                                                                     red                              thiosulfatoethylsulfone                                                                           primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               15     2 moles of 4-aminoanisole-2-                                                                      condensation product of 2 moles of                                                                     claret                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               16     2 moles of 4-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     red                              sulfonylaniline-2-sulfonic                                                                        primary condensation product obtained                     acid                from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               17     2 moles of 4-aminotoluene-2-                                                                      condensation product of 2 moles of                                                                     red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               18     2 moles of 2-aminoanisole-                                                                        condensation product of 2 moles of                                                                     claret                           4-vinylsulfone      primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               19     2 moles of aniline-4-vinyl-                                                                       condensation product of 2 moles of                                                                     red                              sulfone             primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               20     2 moles of aniline-3-vinyl-                                                                       condensation product of 2 moles of                                                                     red                              sulfone             primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               21     2 moles of 2-bromoaniline-4-β-                                                               condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               22     2 moles of 2,6-dichloroaniline-                                                                   condensation product of 2 moles of                                                                     red                              4-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               23     2 moles of 6-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     bluish-tinged                    sulfonyl-2-aminonaphthalene-                                                                      primary condensation product                                                                           redained                         1-sulfonic acid     from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               24     2 moles of 2-naphthylamine-5-                                                                     condensation product of 2 moles of                                                                     red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               25     2 moles of 2-naphthylamine-8-                                                                     condensation product of 2 moles of                                                                     bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product                                                                           redained                                             from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               26     2 moles of 2-naphthylamine-6-                                                                     condensation product of 2 moles of                                                                     bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product                                                                           redained                                             from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               27     2 moles of 2-chloroaniline-                                                                       condensation product of 2 moles of                                                                     red                              4-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               28     2 moles of 2-amino-4-β-                                                                      condensation product of 2 moles of                                                                     red                              sulfatoethylsulfonyl-                                                                             primary condensation product obtained                     benzoic acid        from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               29     2 moles of 5-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     red                              sulfonylaniline-2-sulfonic acid                                                                   primary condensation product obtained                                         from cyanuric chloride and 1-amino-8-                                         naphthol-3,6-disulfonic acid in an                                            equimolar ratio with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               30     2 moles of aniline-4-β-                                                                      condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               31     2 moles of aniline-3-β-                                                                      condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               32     2 moles of aniline-4-β-                                                                      condensation product of 2 moles of                                                                     red                              thiosulfatoethylsulfone                                                                           primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               33     2 moles of aniline-4-vinyl-                                                                       condensation product of 2 moles of                                                                     red                              sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               34     2 moles of 2-aminoanisole-4-                                                                      condensation product of 2 moles of                                                                     claret                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               35     2 moles of 2-methoxy-5-methyl-                                                                    condensation product of 2 moles of                                                                     claret                           aniline-4-β-sulfatoethyl-                                                                    primary condensation product obtained                     sulfone             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               36     2 moles of 2,5-dimethoxy-                                                                         condensation product of 2 moles of                                                                     claret                           aniline-4-β-sulfatoethyl-                                                                    primary condensation product obtained                     sulfone             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               37     2 moles of 8-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     claret                           sulfonyl-2-amino-naphthalene-                                                                     primary condensation product obtained                     6-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               38     2 moles of 6-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     bluish-tinged                    sulfonyl-2-amino-naphthalene-                                                                     primary condensation product                                                                           redained                         1-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               39     2 moles of 2-naphthylamine-6-                                                                     condensation product of 2 moles of                                                                     bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               40     2 moles of 2-naphthylamine-8-                                                                     condensation product of 2 moles of                                                                     bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               41     2 moles of 2-naphthylamine-5-                                                                     condensation product of 2 moles of                                                                     red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-naphthol-4,6-                                          disulfonic acid with 1 mole of 4,4'-                                          diaminostilbene-2,2'-disulfonic acid               42     2 moles of aniline-4-β-                                                                      condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               43     2 moles of aniline-3-β                                                                       condensation product of 2 moles of                                                                     orange                           sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               44     2 moles of aniline-4-vinyl-                                                                       condensation product of 2 moles of                                                                     orange                           sulfone             condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               45     2 moles of aniline-4-β-thio-                                                                 condensation product of 2 moles of                                                                     orange                           sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-napthol-6-sulfonic acid                                         with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               46     2 moles of 2-aminoanisole-4-β-                                                               condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               47     2 moles of aniline-3-vinyl-                                                                       condensation product of 2 moles of                                                                     orange                           sulfone             condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               48     2 moles of 2-aminoanisole-4-                                                                      condensation product of 2 moles of                                                                     red                              β-thiosulfatoethylsulfone                                                                    condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               49     2 moles of 2,5-dimethoxyaniline-                                                                  condensation product of 2 moles of                                                                     bluish-tinged                    4-β-sulfatoethylsulfone                                                                      condensation product obtained                                                                          redm                                                 equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               50     2 moles of 2-methoxy-5-methyl-                                                                    condensation product of 2 moles of                                                                     red                              aniline-4-β-sulfatoethyl-                                                                    condensation product obtained from                        sulfone             equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               51     2 moles of 2-aminonaphthalene-                                                                    condensation product of 2 moles of                                                                     red                              8-β-sulfatoethylsulfone                                                                      condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               52     2 moles of 2-aminonaphthalene-                                                                    condensation product of 2 moles of                                                                     red                              6-β-sulfatoethylsulfone                                                                      condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               53     2 moles of 2-aminonaphthalene-                                                                    condensation product of 2 moles of                                                                     red                              5-β-sulfatoethylsulfone                                                                      condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               54     2 moles of aniline-4-β-                                                                      condensation product of 2 moles of                                                                     orange                           sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               55     2 moles of aniline-4-β-thio-                                                                 condensation product of 2 moles of                                                                     orange                           sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               56     2 moles of aniline-3-vinyl-                                                                       condensation product of 2 moles of                                                                     orange                           sulfone             condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               57     2 moles of aniline-3-β-                                                                      condensation product of 2 moles of                                                                     orange                           sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               58     2 moles of 2-aminoanisole-4-                                                                      condensation product of 2 moles of                                                                     reddish-                         β-sulfatoethylsulfone                                                                        condensation product obtained                                                                          tinged orange                                        equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               59     2 moles of 2-aminoanisole-4-                                                                      condensation product of 2 moles of                                                                     reddish-                         β-thiosulfatoethylsulfone                                                                    condensation product obtained                                                                          tinged orange                                        equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               60     2 moles of 2-aminoanisole-5-                                                                      condensation product of 2 moles of                                                                     red                              β-sulfatoethylsulfone                                                                        condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               61     2 moles of 2-methoxy-5-methyl-                                                                    condensation product of 2 moles of                                                                     red                              aniline-4-β-sulfatoethyl-                                                                    condensation product obtained from                        sulfone             equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               62     2 moles of 2,5-dimethoxyaniline-                                                                  condensation product of 2 moles of                                                                     red                              4-β-sulfatoethylsulfone                                                                      condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               63     2 moles of 2-aminonaphthalene-                                                                    condensation product of 2 moles of                                                                     reddish-                         8-β-sulfatoethylsulfone                                                                      condensation product obtained                                                                          tinged orange                                        equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               64     2 moles of 8-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     reddish-                         sulfonyl-2-amino-naphthalene-                                                                     condensation product obtained                                                                          tinged orange                    6-sulfonic acid     equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               65     2 moles of 6-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     orange                           sulfonyl-2-amino-naphthalene-                                                                     condensation product obtained from                        1-sulfonic acid     equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 4,4'-diaminostilbene-                                          2,2'-disulfonic acid                               66     2 moles of aniline-4-β-                                                                      condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric bromide                                         and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      67     2 moles of aniline-3-β-                                                                      condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric bromide                                         and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      68     2 moles of aniline-4-β-                                                                      condensation product of 2 moles of                                                                     red                              thiosulfatoethylsulfone                                                                           condensation product obtained from                                            equimolar amounts of cyanuric bromide                                         and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      69     2 moles of aniline-3-vinyl-                                                                       condensation product of 2 moles of                                                                     red                              sulfone             condensation product obtained from                                            equimolar amounts of cyanuric bromide                                         and 1 amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      70     2 moles of 2-aminoanisole-4-                                                                      condensation product of 2 moles of                                                                     claret                           β-sulfatoethylsulfone                                                                        condensation product obtained from                                            equimolar amounts of cyanuric bromide                                         and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2' -disulfonic acid                     71     2 moles of 2-aminoanisole-4-β-                                                               condensation product of 2 moles of                                                                     claret                           thiosulfatoethylsulfone                                                                           condensation product obtained from                                            equimolar amounts of cyanuric bromide                                         and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      72     2 moles of 2-aminoanisole-5-β-                                                               condensation product of 2 moles of                                                                     bluish-tinged                    sulfatoethylsulfone condensation product obtained                                                                          redm                                                 equimolar amounts of cyanuric bromide                                         and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      73     2 moles of 2,5-dimethoxy-                                                                         condensation product of 2 moles of                                                                     claret                           aniline-4-β-sulfatoethyl-                                                                    condensation product obtained from                        sulfone             equimolar amounts of cyanuric bromide                                         and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      74     2 moles of 2-methoxy-5-methyl-                                                                    condensation product of 2 moles of                                                                     claret                           aniline-4-β-sulfatoethyl                                                                     condensation product obtained from                        sulfone             equimolar amounts of cyanuric bromide                                         and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      75     2 moles of 8-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     claret                           sulfonyl-2-aminonaphthalene-                                                                      condensation product obtained from                        6-sulfonic acid     equimolar amounts of cyanuric bromide                                         and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      76     2 moles of 6-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     bluish-tinged                    sulfonyl-2-aminonaphthalene-                                                                      condensation product obtained                                                                          redm                             1-sulfonic acid     equimolar amounts of cyanuric bromide                                         and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      77     2 moles of aniline-4-β-                                                                      condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric fluoride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      78     2 moles of aniline-3-β-                                                                      condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric fluoride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      79     2 moles of 2-aminoanisole-4-                                                                      condensation product of 2 moles of                                                                     claret                           β-sulfatoethylsulfone                                                                        condensation product obtained from                                            equimolar amounts of cyanuric fluoride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      80     2 moles of aniline-4-β-thio-                                                                 condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric fluoride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      81     2 moles of aniline-4-vinyl-                                                                       condensation product of 2 moles of                                                                     red                              sulfone             condensation product obtained from                                            equimolar amounts of cyanuric fluoride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      82     2 moles of aniline-3-vinyl-                                                                       condensation product of 2 moles of                                                                     red                              sulfone             condensation product obtained from                                            equimolar amounts of cyanuric fluoride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                      83     2 moles of 2-aminoanisole-4-                                                                      condensation product of 2 moles of                                                                     claret                           β-thiosulfatoethylsulfone                                                                    condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 3,3'-dimethoxy-                                           benzidine-6,6'-disulfonic acid                     84     2 moles of 2,5-dimethoxyaniline-                                                                  condensation product of 2 moles of                                                                     claret                           4-β-sulfatoethylsulfone                                                                      condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 3,3'-dimethoxy-                                           benzidine-6,6'-disulfonic acid                     85     2 moles of 2-methoxy-5-methyl-                                                                    condensation product of 2 moles of                                                                     claret                           aniline-4-β-sulfatoethylsulfone                                                              condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 3,3'-dimethoxy-                                           benzidine-6,6'-disulfonic acid                     86     2 moles of 8-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     claret                           sulfonyl-2-amino-naphthalene-                                                                     condensation product obtained from                        6-sulfonic acid     equimolar amounts of cyanuric chloride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 3,3'-dimethoxy-                                           benzidine-6,6'-disulfonic acid                     87     2 moles of 6-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     bluish-tinged                    sulfonyl-2-amino-naphthalene-                                                                     condensation product obtained                                                                          redm                             1-sulfonic acid     equimolar amounts of cyanuric chloride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 3,3'-dimethoxy-                                           benzidine-6,6'-disulfonic acid                     88     2 moles of aniline-4-β-                                                                      condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 3,3'-dimethoxy-                                           benzidine-6,6'-disulfonic acid                     89     2 moles of aniline-4-β-thio-                                                                 condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 3,3'-dimethoxy-                                           benzidine-6,6'-disulfonic acid                     90     2 moles of aniline-3-β-                                                                      condensation product of 2 moles of                                                                     red                              sulfatoethylsulfone condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 1-amino-8-naphthol-3,6-disulfonic                                         acid with 1 mole of 3,3'-dimethoxy-                                           benzidine-6,6'-disulfonic acid                     91     2 moles of 2-aminoanisole-4-                                                                      condensation product of 2 moles of                                                                     orange                           β-sulfatoethylsulfone                                                                        condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 3,3'-dimethoxy-6,6'-                                           disulfonic acid                                    92     2 moles of 2-methoxy-5-methyl-                                                                    condensation product of 2 moles of                                                                     red                              aniline-4-β-sulfatoethyl-                                                                    condensation product obtained from                        sulfone             equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 3,3'-dimethoxy-6,6'-                                           disulfonic acid                                    93     2 moles of aniline-4-β-sulfato-                                                              condensation product of 2 moles of                                                                     orange                           ethylsulfone        condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 3,3'-dimethoxy-6,6'-                                           disulfonic acid                                    94     2 moles of 8-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     red                              sulfonyl-2-amino-naphthalene-                                                                     condensation product obtained from                        6-sulfonic acid     equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 3,3'-dimethoxy-6,6'-                                           disulfonic acid                                    95     2 moles of 6-β-sulfatoethyl-                                                                 condensation product of 2 moles of                                                                     red                              sulfonyl-2-amino-naphthalene                                                                      condensation product obtained from                        1-sulfonic acid     equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 3,3'-dimethoxy-6,6'-                                           disulfonic acid                                    96     2 moles of 2,5-dimethoxyaniline-                                                                  condensation product of 2 moles of                                                                     bluish-tinged                    4-β-sulfatoethylsulfone                                                                      condensation product obtained                                                                          redm                                                 equimolar amounts of cyanuric chloride                                        and 2-amino-8-naphthol-6-sulfonic acid                                        with 1 mole of 3,3'-dimethoxy-6,6'-                                           disulfonic acid                                    97     2 moles of aniline-4-β-sulfato-                                                              condensation product of 2 moles of the                                                                 orange                           ethylsulfone        condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 3,3'-dimethoxy-                                                benzidine-6,6'-disulfonic acid                     98     2 moles of 2-aminoanisole-4-                                                                      condensation product of 2 moles of                                                                     reddish-                         β-thiosulfatoethylsulfone                                                                    condensation product obtained                                                                          tinged orange                                        equimolar amounts of cyanuric chloride                                        with 1 mole of 3,3'-dimethoxy-                                                benzidine-6,6'-disulfonic acid                     99     2 moles of aniline-3-vinyl-                                                                       condensation product of 2 moles of                                                                     orange                           sulfone             condensation product obtained from                                            equimolar amounts of cyanuric                                                                          and                                                                           2-amino-5-naphthol-7-s                                                        ulfonic acid                                         with 1 mole of 3,3'-dimethoxy-                                                benzidine-6,6'-disulfonic acid                     100    2 moles of 2,6-dimethylaniline-                                                                   condensation product of 2 moles of the                                                                 orange                           4-β-sulfatoethylsulfone                                                                      condensation product obtained from                                            equimolar amounts of cyanuric chloride                                        and 2-amino-5-naphthol-7-sulfonic acid                                        with 1 mole of 3,3'dimethoxy-                                                 benzidine-6,6'-disulfonic acid                     101    2 moles of aniline-4-β-sulfato-                                                              reaction product of 2 moles of                                                                         red                              ethylsulfone        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        102    2 moles of aniline-4-β-chloro-                                                               reaction product of 2 moles of                                                                         red                              ethylsulfone        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        103    2 moles of aniline-3-β-sulfato-                                                              reaction product of 2 moles of                                                                         red                              ethylsulfone        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        104    2 moles of 2-aminoanisole-5-                                                                      reaction product of 2 moles of                                                                         claret                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        105    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         claret                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        106    2 moles of 2-aminotoluene-4-                                                                      reaction product of 2 moles of                                                                         red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        107    2 moles of 2-methoxy-5-methyl-                                                                    reaction product of 2 moles of                                                                         claret                           aniline-4-β-sulfatoethyl-                                                                    primary condensation product obtained                     sulfone             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        108    2 moles of 2,5-dimethoxy-                                                                         reaction product of 2 moles of                                                                         claret                           aniline-4-β-sulfatoethyl-                                                                    primary condensation product obtained                     sulfone             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        109    2 moles of 2-chloroaniline-5-                                                                     reaction product of 2 moles of                                                                         red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        110    2 moles of 2,6-dimethylaniline-                                                                   reaction product of 2 moles of                                                                         red                              4-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        111    2 moles of 2,6-dimethylaniline-                                                                   reaction product of 2 moles of                                                                         red                              3-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        112    2 moles of 2,4-dimethoxy-                                                                         reaction product of 2 moles of                                                                         bluish-tinged                    aniline-5-β-sulfatoethyl-                                                                    primary condensation product                                                                           redained                         sulfone             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        113    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         claret                           β-thiosulfatoethylsulfone                                                                    primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        114    2 moles of aniline-4-β-thio-                                                                 reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        115    2 moles of 4-aminoanisole-2-                                                                      reaction product of 2 moles of                                                                         red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphhthalene-3,6-disulfonic acid with                                         1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        116    2 moles of 4-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         red                              sulfonylaniline-2-sulfonic                                                                        primary condensation product obtained                     acid                from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,1-bis-(4'-aminophenyl)-                                           cyclohexane                                        117    2 moles of 4-aminotoluene-2-                                                                      reaction product of 2 moles of                                                                         orange                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1 mole                                       of 1,1-bis-(4'-amino-3'-sulfophenyl)-                                         cyclohexane                                        118    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         yellowish-                       vinylsulfone        primary condensation product                                                                           tinged red                                           from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1                                            mole of 1,1-bis-(4'-amino-3'-sulfo-                                           phenyl)-cyclohexane                                119    2 moles of aniline-4-vinyl                                                                        reaction product of 2 moles of                                                                         orange                           sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1                                            mole of 1,1-bis-(4'-amino-3'-sulfo-                                           phenyl)-cyclohexane                                120    2 moles of aniline-3-vinyl-                                                                       reaction product of 2 moles of                                                                         orange                           sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1                                            mole of 1,1-bis-(4'-amino-3'-sulfo-                                           phenyl)-cyclohexane                                121    2 moles of 2-bromoaniline-4-                                                                      reaction product of 2 moles of                                                                         orange                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphhthalene-6-sulfonic acid with 1                                           mole of 1,1-bis-(4'-amino-3'-sulfo-                                           phenyl)-cyclohexane                                122    2 moles of 2,6-dichloroaniline-                                                                   reaction product of 2 moles of                                                                         orange                           4-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1                                            mole of 1,1-bis-(4'-amino-3'-sulfo-                                           phenyl)-cyclohexane                                123    2 moles of 6-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         yellowish-                       sulfonyl-2-amino-naphthalene-                                                                     primary condensation product                                                                           tinged red                       1-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1                                            mole of 1,1-bis-(4'-amino-3'-sulfo-                                           phenyl)-cyclohexane                                124    2 moles of 2-naphthylamine-5-                                                                     reaction product of 2 moles of                                                                         orange                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1                                            mole of 1,1-bis-(4'-amino-3'-sulfo-                                           phenyl)-cyclohexane                                125    2 moles of 2-naphthylamine-8-                                                                     reaction product of 2 moles of                                                                         yellowish-                       β-sulfatoethylsulfone                                                                        primary condensation product                                                                           tinged red                                           from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1                                            mole of 1,1-bis-(4'-amino-3'-sulfo-                                           phenyl)-cyclohexane                                126    2 moles of 2-naphthylamine-6-                                                                     reaction product of 2 moles of                                                                         yellowish-                       β-sulfatoethylsulfone                                                                        primary condensation product                                                                           tinged red                                           from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1                                            mole of 1,1-bis-(4'-amino-3'-sulfo-                                           phenyl)-cyclohexane                                127    2 moles of 2-chloroaniline-4-                                                                     reaction product of 2 moles of                                                                         orange                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1                                            mole of 1,1-bis-(4'-amino-3' -sulfo-                                          phenyl)-cyclohexane                                128    2 moles of 2-amino-4-β-                                                                      reaction product of 2 moles of                                                                         orange                           sulfatoethylsulfonyl-                                                                             primary condensation product obtained                     benzoic acid        from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1                                            mole of 1,1-bis-(4'-amino-3'-sulfo-                                           phenyl)-cyclohexane                                129    2 moles of 5-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         orange                           sulfonyl-aniline-2-sulfonic                                                                       primary condensation product obtained                     acid                from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid with 1                                            mole of 1,1-bis-(4'-amino-3'-sulfo-                                           phenyl)-cyclohexane                                130    2 moles of aniline-4-β-                                                                      reaction product of 2 moles of                                                                         orange                           sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-5-hydroxy-                                               naphthalene-7-sulfonic acid with 1                                            mole of 4,4'-diaminodiphenylamine-2-                                          sulfonic acid                                      131    2 moles of aniline-3-β-                                                                      reaction product of 2 moles of                                                                         orange                           sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-5-hydroxy-                                               naphthalene-7-sulfonic acid with 1                                            mole of 4,4'-diaminodiphenylamine-2-                                          sulfonic acid                                      132    2 moles of aniline-4-β-thio-                                                                 reaction product of 2 moles of                                                                         orange                           sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-5-hydroxy-                                               naphthalene-7-sulfonic acid with 1                                            mole of 4,4'diaminodiphenylamine-2-                                           sulfonic acid                                      133    2 moles of aniline-4-vinyl-                                                                       reaction product of 2 moles of                                                                         orange                           sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-5-hydroxy-                                               naphthalene-7-sulfonic acid with 1                                            mole of 4,4'-diaminodiphenylamine-2-                                          sulfonic acid                                      134    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product of                                                                        redi-                                                molar amounts of cyanuric chloride                                            and 1-amino-8-hydroxynaphthalene-                                             4,6-disulfonic acid with 1 mole of                                            1,6-diaminohexane                                  135    2 moles of 2-methoxy-5-methyl-                                                                    reaction product of 2 moles of                                                                         bluish-tinged                    aniline-4-β-sulfatoethylsulfone                                                              primary condensation product of                                                                        redi-                                                molar amounts of cyanuric chloride                                            and 1-amino-8-hydroxynaphthalene-                                             4,6-disulfonic acid with 1 mole of                                            1,6-diaminohexane                                  136    2 moles of 2,5-dimethoxyaniline-                                                                  reaction product of 2 moles of                                                                         claret                           4-β-sulfatoethylsulfone                                                                      primary condensation product of equi-                                         molar amounts of cyanuric chloride                                            and 1-amino-8-hydroxynaphthalene-                                             4,6-disulfonic acid with 1 mole of                                            1,6-diaminohexane                                  137    2 moles of 8-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         bluish-tinged                    sulfonyl-2-amino-naphthalene-                                                                     primary condensation product of                                                                        redi-                            6-sulfonic acid     molar amounts of cyanuric chloride                                            and 1-amino-8-hydroxynaphthalene-                                             4,6-disulfonic acid with 1 mole of                                            1,6-diaminohexane                                  138    2 moles of 6-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         bluish-tinged                    sulfonyl-2-amino-naphthalene-                                                                     primary condensation product of                                                                        redi-                            1-sulfonic acid     molar amounts of cyanuric chloride                                            and 1-amino-8-hydroxynaphthalene-                                             4,6-disulfonic acid with 1 mole of                                            1,6-diaminohexane                                  139    2 moles of 2-naphthylamine-6-                                                                     reaction product of 2 moles of                                                                         bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product of                                                                        redi-                                                molar amounts of cyanuric chloride                                            and 1-amino-8-hydroxynaphthalene-                                             4,6-disulfonic acid with 1 mole of                                            1,6-diaminohexane                                  140    2 moles of 2-naphthylamine-8-                                                                     reaction product of 2 moles of                                                                         bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product of                                                                        redi-                                                molar amounts of cyanuric chloride                                            and 1-amino-8-hydroxynaphthalene-                                             4,6-disulfonic acid with 1 mole of                                            1,6-diaminohexane                                  141    2 moles of 2-naphthylamine-5-                                                                     reaction product of 2 moles of                                                                         bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product of                                                                        redi-                                                molar amounts of cyanuric chloride                                            and 1-amino-8-hydroxynaphthalene-                                             4,6-disulfonic acid with 1 mole of                                            1,6-diaminohexane                                  142    2 moles of aniline-4-β-sulfato-                                                              reaction product of 2 moles of                                                                         red                              ethylsulfone        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,4-diaminobutane                        143    2 moles of aniline-3-β-                                                                      reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,4-diaminobutane                        144    2 moles of aniline-4-vinyl-                                                                       reaction product of 2 moles of                                                                         red                              sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,4-diaminobutane                        145    2 moles of aniline-4-β-thio-                                                                 reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,4-diaminobutane                        146    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,4-diaminobutane                        147    2 moles of aniline-3-vinyl-                                                                       reaction product of 2 moles of                                                                         red                              sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,4-diaminobutane                        148    2 moles of 2-aminoanisole-4-β-                                                               reaction product of 2 moles of                                                                         bluish-tinged                    thiosulfatoethylsulfone                                                                           primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,4-diaminobutane                        149    2 moles of 2,5-dimethoxyaniline-                                                                  reaction product of 2 moles of                                                                         claret                           4-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,4-diaminobutane                        150    2 moles of 2-methoxy-5-methyl-                                                                    reaction product of 2 moles of                                                                         yellowish-                       aniline-4-β-sulfatoethyl-                                                                    primary condensation product                                                                           tinged red                       sulfone             from equimolar amounts of cyanuric                                            chloride and 2-amino-5-hydroxy-                                               naphthalene-1,7-disulfonic acid and                                           1 mole of 1,2-diaminoethane                        151    2 moles of 2-aminonaphthalene-                                                                    reaction product of 2 moles of                                                                         yellowish-                       8-β-sulfatoethylsulfone                                                                      primary condensation product                                                                           tinged red                                           from equimolar amounts of cyanuric                                            chloride and 2-amino-5-hydroxy-                                               naphthalene-1,7-disulfonic acid and                                           1 mole of 1,2-diaminoethane                        152    2 moles of 2-aminonaphthalene-                                                                    reaction product of 2 moles of                                                                         yellowish-                       6-β-sulfatoethylsulfone                                                                      primary condensation product                                                                           tinged red                                           from equimolar amounts of cyanuric                                            chloride and 2-amino-5-hydroxy-                                               naphthalene-1,7-disulfonic acid and                                           1 mole of 1,2-diaminoethane                        153    2 moles of 2-aminonaphthalene-                                                                    reaction product of 2 moles of                                                                         yellowish-                       5-β-sulfatoethylsulfone                                                                      primary condensation product                                                                           tinged red                                           from equimolar amounts of cyanuric                                            chloride and 2-amino-5-hydroxy-                                               naphthalene-1,7-disulfonic acid and                                           1 mole of 1,2-diaminoethane                        154    2 moles of aniline-4-β-sulfato-                                                              reaction product of 2 moles of                                                                         red                              ethylsulfone        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        155    2 moles of aniline-4-β-thio-                                                                 reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        156    2 moles of aniline-3-vinyl-                                                                       reaction product of 2 moles of                                                                         red                              sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        157    2 moles of aniline-3-β-sulfato-                                                              reaction product of 2 moles of                                                                         red                              ethylsulfone        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        158    2 moles of 2-aminoanisole-4-β-                                                               reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar anounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        159    2 moles of 2-aminoanisole-4-β -                                                              reaction product of 2 moles of                                                                         red                              thiosulfatoethylsulfone                                                                           primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        160    2 moles of 2-aminoanisole-5-β-                                                               reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        161    2 moles of 2-methoxy-5-methyl-                                                                    reaction product of 2 moles of                                                                         bluish-tinged                    aniline-4-β-sulfatoethylsulfone                                                              primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        162    2 moles of 2,5-dimethoxyaniline-                                                                  reaction product of 2 moles of                                                                         bluish-tinged                    4-β-sulfatoethylsulfone                                                                      primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        163    2 moles of 2-aminonaphthalene-                                                                    reaction product of 2 moles of                                                                         red                              8-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        164    2 moles of 8-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         red                              sulfonyl-2-amino-naphthalene-                                                                     primary condensation product obtained                     6-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        165    2 moles of 6-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         red                              sulfonyl-2-amino-naphthalene-                                                                     primary condensation product obtained                     1-sulfonic acid     from equimolar anounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,3-bis-aminomethyl-                                                cyclohexane                                        166    2 moles of aniline-4-β-sulfato-                                                              reaction product of 2 moles of                                                                         red                              ethylsulfone        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4-sulfonic acid with                                              1 mole of 3,3'-dimethyl-4,4'-diamino-di-                                      phenyl-6,6'-disulfonic acid                        167    2 moles of aniline-3-β-                                                                      reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4-sulfonic acid with                                              1 mole of 3,3'-dimethyl-4,4'-diamino-di-                                      phenyl-6,6'-disulfonic acid                        168    2 moles of aniline-4-β-                                                                      reaction product of 2 moles of                                                                         red                              thiosulfatoethylsulfone                                                                           primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4-sulfonic acid with                                              1 mole of 3,3'-dimethyl-4,4'-diamino-di-                                      phenyl-6,6'-disulfonic acid                        169    2 moles of aniline-3-vinyl-                                                                       reaction product of 2 moles of                                                                         red                              sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4-sulfonic acid with                                              1 mole of 3,3'-dimethyl-4,4'-diamino-di-                                      phenyl-6,6'-disulfonic acid                        170    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4-sulfonic acid with                                              1 mole of 3,3'-dimethyl-4,4'-diamino-di-                                      phenyl-6,6'-disulfonic acid                        171    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         red                              β-thiosulfatoethylsulfone                                                                    primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4-sulfonic acid with                                              1 mole of 3,3'-dimethyl-4,4'-diamino-di-                                      phenyl-6,6'-disulfonic acid                        172    2 moles of 2-aminoanisole-5-                                                                      reaction product of 2 moles of                                                                         red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4-sulfonic acid with                                              1 mole of 3,3'-dimethyl-4,4'-diamino-di-                                      phenyl-6,6'-disulfonic acid                        173    2 moles of 2,5-dimethoxyaniline-                                                                  reaction product of 2 moles of                                                                         red                              4-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4-sulfonic acid with                                              1 mole of 3,3'-dimethyl-4,4'-diamino-di-                                      phenyl-6,6'-disulfonic acid                        174    2 moles of 2-methoxy-5-methyl-                                                                    reaction product of 2 moles of                                                                         red                              aniline-4-β-sulfatoethylsulfone                                                              primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4-sulfonic acid with                                              1 mole of 3,3'-dimethyl-4,4'-diamino-di-                                      phenyl-6,6'-disulfonic acid                        175    2 moles of 8-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         red                              sulfonyl-2-aminonaphthalene-                                                                      primary condensation product obtained                     6-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4-sulfonic acid with                                              1 mole of 3,3'-dimethyl-4,4'-diamino-di-                                      phenyl-6,6'-disulfonic acid                        176    2 moles of 6-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         red                              sulfonyl-2-aminonaphthalene-                                                                      primary condensation product obtained                     1-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4-sulfonic acid with                                              1 mole of 3,3'-dimethyl-4,4'-diamino-di-                                      phenyl-6,6'-disulfonic acid                        177    2 moles of aniline-4-β-                                                                      reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and ammonia with                                          1 mole of 4,4'-diaminostilbene-2,2'-                                          disulfonic acid                                    178    2 moles of aniline-3-β-sulfato-                                                              reaction product of 2 moles of                                                                         red                              ethylsulfone        secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and ammonia with                                          1 mole of 4,4'-diaminostilbene-2,2'-                                          disulfonic acid                                    179    2 moles of 2-aminoanisole-4-β-                                                               reaction product of 2 moles of                                                                         bluish-tinged                    sulfatoethylsulfone secondary condensation product                                                                         redained                                             from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and ammonia with                                          1 mole of 4,4'-diaminostilbene-2,2'-                                          disulfonic acid                                    180    2 moles of aniline-β-thio-                                                                   reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and ammonia with                                          1 mole of 4,4'-diaminostilbene-2,2'-                                          disulfonic acid                                    181    2 moles of aniline-4-vinyl-                                                                       reaction product of 2 moles of                                                                         red                              sulfone             secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and ammonia with                                          1 mole of 4,4'-diaminostilbene-2,2'-                                          disulfonic acid                                    182    2 moles of aniline-3-vinyl-                                                                       reaction product of 2 moles of                                                                         red                              sulfone             secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and ammonia with                                          1 mole of 4,4'-diaminostilbene-2,2'-                                          disulfonic acid                                    183    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         red                              β-thiosulfatoethylsulfone                                                                    primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4,6-disulfonic acid with                                          1 mole of 1,4-diaminobenzene-3,6-                                             disulfonic acid                                    184    2 moles of 2,5-dimethoxy-                                                                         reaction product of 2 moles of                                                                         claret                           aniline-4-β-sulfatoethylsulfone                                                              primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4,6-disulfonic acid with                                          1 mole of 1,4-diaminobenzene-3,6-                                             disulfonic acid                                    185    2 moles of 2-methoxy-5-methyl-                                                                    reaction product of 2 moles of                                                                         claret                           aniline-4-β-sulfatoethylsulfone                                                              primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4,6-disulfonic acid with                                          1 mole of 1,4-diaminobenzene-3,6-                                             disulfonic acid                                    186    2 moles of 8-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         bluish-tinged                    sulfonyl-2-amino-naphthalene-                                                                     primary condensation product                                                                           redained                         6-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4,6-disulfonic acid with                                          1 mole of 1,4-diaminobenzene-3,6-                                             disulfonic acid                                    187    2 moles of 6-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         bluish-tinged                    sulfonyl-2-amino-naphthalene-                                                                     primary condensation product                                                                           redained                         1-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4,6-disulfonic acid with                                          1 mole of 1,4-diaminobenzene-3,6-                                             disulfonic acid                                    188    2 moles of aniline-4-β-sulfato-                                                              reaction product of 2 moles of                                                                         orange                           ethylsulfone        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-methylamino-5-hydroxy-                                         naphthalene-7-sulfonic acid with                                              1 mole of di-(3-amino-4-sulfophenyl)-                                         sulfone                                            189    2 moles of aniline-4-β-thio-                                                                 reaction product of 2 moles of                                                                         orange                           sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-methylamino-5-hydroxy-                                         naphthalene-7-sulfonic acid with                                              1 mole of di-(3-amino-4-sulfophenyl)-                                         sulfone                                            190    2 moles of aniline-3-β-                                                                      reaction product of 2 moles of                                                                         orange                           sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-methylamino-5-hydroxy-                                         naphthalene-7-sulfonic acid with                                              1 mole of di-(3-amino-4-sulfophenyl)-                                         sulfone                                            191    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         orange                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-methylamino-5-hydroxy-                                         naphthalene-7-sulfonic acid with                                              1 mole of di-(3-amino-4-sulfophenyl)-                                         sulfone                                            192    2 moles of 2-methoxy-5-methyl-                                                                    reaction product of 2 moles of                                                                         reddish-                         aniline-4-β-sulfatoethylsulfone                                                              primary condensation product                                                                           tinged orange                                        from equimolar amounts of cyanuric                                            chloride and 2-methylamino-5-hydroxy-                                         naphthalene-7-sulfonic acid with                                              1 mole of di-(3-amino-4-sulfophenyl)-                                         sulfone                                            193    2 moles of aniline-4-β-sulfato-                                                              reaction product of 2 moles of                                                                         red                              ethylsulfone        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 4,4'-diamino-diphenyl-sulfone            194    2 moles of 8-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         bluish-tinged                    sulfonyl-2-amino-naphthalene-                                                                     primary condensation product                                                                           redained                         6-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 4,4'-diamino-diphenyl-sulfone            195    2 moles of 6-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         bluish-tinged                    sulfonyl-2-amino-naphthalene-                                                                     primary condensation product                                                                           redained                         1-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 4,4'-diamino-diphenyl-sulfone            196    2 moles of 2,5-dimethoxy-                                                                         reaction product of 2 moles of                                                                         claret                           aniline-4-β-sulfatoethyl-                                                                    primary condensation product obtained                     sulfone             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4,6-disulfonic acid with                                          1 mole of 4,4'-diamino-diphenylure-                                           3,3'-disulfonic acid                               197    2 moles of aniline-4-β-                                                                      reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and aniline-3-                                            sulfonic acid with 1 mole of 2,2'-di-                                         chloro-4,4'-diaminodiphenyl                        198    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         bluish-tinged                    β-thiosulfatoethylsulfone                                                                    secondary condensation product                                                                         redained                                             from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and aniline-3-                                            sulfonic acid with 1 mole of 2,2'-di-                                         chloro-4,4'-diaminodiphenyl                        199    2 moles of aniline-3-vinyl-                                                                       reaction product of 2 moles of                                                                         red                              sulfone             secondary condensation product obtained                                       from equimolar amounts of cyanuric chloride,                                  1-amino-8-hydroxynaphthalene-3,6-disul-                                       fonic acid and 2-amino-ethanol with 1 mole                                    of 4,4'-diaminodiphenyl-3,3'-dicarboxylic                                     acid                                               200    2 moles of 2,6-dimethylaniline-                                                                   reaction product of 2 moles of                                                                         red                              4-β-sulfatoethylsulfone                                                                      secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and β-sulfatoethyl-                                  amine with 1 mole of 2,7-diamino-                                             carbazole                                          201    2 moles of aniline-4-β-                                                                      reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and isopropanol                                           with 1 mole of 3-ethoxy-4,4'-diamino-                                         diphenyl                                           202    2 moles of aniline-3-β-                                                                      reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and isopropanol                                           with 1 mole of 3-ethoxy-4,4'-diamino-                                         diphenyl                                           203    2 moles of aniline-3-β-                                                                      reaction product of 2 moles of                                                                         red                              sulfatoethylsulfone secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       4,6-disulfonic acid and thioglycollic                                         acid with 1 mole of 3,3'-dichloro-4,4'-                                       diamino-diphenyl                                   204    2 moles of 2-aminoanisole-                                                                        reaction product of 2 moles of                                                                         bluish-tinged                    5-β-sulfatoethylsulfone                                                                      secondary condensation product                                                                         redained                                             from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       4,6-disulfonic acid and thioglycollic                                         acid with 1 mole of 3,3'-dichloro-4,4'-                                       diamino-diphenyl                                   205    2 moles of 2-aminoanisole-4-β-                                                               reaction product of the  orange                           sulfatoethylsulfone secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 2-amino-5-hydroxynaphthalene-                                       7-sulfonic acid and methyltaurine with                                        1 mole of 2,7-diaminodiphenylsulfone               206    2 moles of 2-aminotoluene-4-                                                                      reaction product of 2 moles of                                                                         orange                           β-sulfatoethylsulfone                                                                        secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 2-amino-5-hydroxynaphthalene-                                       7-sulfonic acid and methyltaurine with                                        1 mole of 2,7-diaminodiphenylsulfone               207    2 moles of 2-methoxy-5-methyl-                                                                    reaction product of 2 moles of                                                                         red                              aniline-4-β-sulfatoethyl-                                                                    secondary condensation product obtained                   sulfone             from equimolar amounts of cyanuric                                            chloride, 2-amino-8-hydroxynaphthalene-                                       6-sulfonic acid and β-aminopropionic                                     acid with 1 mole of 2,2'-dichloro-5,5'-                                       dimethoxy-4,4'-diaminodiphenyl                     208    2 moles of 2,5-dimethoxy-                                                                         reaction product of 2 moles of                                                                         claret                           aniline-4-β-sulfatoethyl-                                                                    secondary condensation product obtained                   sulfone             from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and β-methoxyethyl-                                  amine with 1 mole of 2,2'-dimethoxy-                                          5,5'-disulfo-4,4'-diamino-diphenylurea             209    2 moles of 2-chloroaniline-                                                                       reaction product of 2 moles of                                                                         red                              5-β-sulfatoethylsulfone                                                                      secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and β-methoxyethyl-                                  amine with 1 mole of 2,2'-dimethoxy-                                          5,5'-disulfo-4,4'-diamino-diphenylurea             210    2 moles of 2,6-dimethylaniline-                                                                   reaction product of 2 moles of                                                                         red                              4-β-sulfatoethylsulfone                                                                      secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       4,6-disulfonic acid and aniline-N-                                            methanesulfonic acid with 1 mole of                                           benzidine                                          211    2 moles of 2,6-dimethylaniline-                                                                   reaction product of 2 moles of                                                                         red                              3-β-sulfatoethylsulfone                                                                      secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       4,6-disulfonic acid and aniline-N-                                            methanesulfonic acid with 1 mole of                                           benzidine                                          212    2 moles of 2,4-dimethoxyaniline-                                                                  reaction product of 2 moles of                                                                         claret                           5-β-sulfatoethylsulfone                                                                      secondary condensation product obtained                                       from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and p-aminobenzoic                                        acid with 1 mole of 4,4'-diamino-                                             diphenyl-sulfide-2,2'-disulfonic acid              213    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         bluish-tinged                    β-thiosulfatoethylsulfone                                                                    secondary condensation product                                                                         redained                                             from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and p-aminobenzoic                                        acid with 1 mole of 4,4'-diamino-                                             diphenyl-sulfide-2,2'-disulfonic acid              214    2 moles of aniline-4-β-thio-                                                                 reaction product of 2 moles of                                                                         bluish-tinged                    sulfatoethylsulfone secondary condensation product                                                                         redained                                             from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and aniline-2,5-                                          disulfonic acid with 1 mole of 2,5-                                           bis-(4'-aminophenyl)-1,3,4-oxadiazole              215    2 moles of 4-aminoanisole-2-                                                                      reaction product of 2 moles of                                                                         bluish-tinged                    β-sulfatoethylsulfone                                                                        secondary condensation product                                                                         redained                                             from equimolar amounts of cyanuric                                            chloride, 1-amino-8-hydroxynaphthalene-                                       3,6-disulfonic acid and aniline-2,5-                                          disulfonic acid with 1 mole of 2,5-                                           bis-(4'-aminophenyl)-1,3,4-oxadiazole              216    2 moles of 4-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         red                              sulfonyl-aniline-2-sulfonic                                                                       secondary condensation product                            acid                obtained from equimolar amounts of                                            cyanuric chloride, 1-amino-8-hydroxy-                                         naphthalene-3,6-disulfonic acid and                                           aniline-2,5-disulfonic acid with 1                                            mole of 2,5-bis-(4'-aminophenyl)-                                             1,3,4-oxadiazole                                   217    2 moles of 4-aminotoluene-                                                                        reaction product of 2 moles of                                                                         red                              2-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4,6-disulfonic acid with                                          1 mole of 4,4'-diamino-2-sulfo-                                               diphenyl ether                                     218    2 moles of 2-aminoanisole-                                                                        reaction product of 2 moles of                                                                         bluish-tinged                    4-vinyl-sulfone     primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4,6-disulfonic acid with                                          1 mole of 4,4'-diamino-2-sulfo-                                               diphenyl ether                                     219    2 moles of aniline-4-vinyl-                                                                       reaction product of 2 moles of                                                                         red                              sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,5-diaminonaphthalene                   220    2 moles of aniline-3-vinyl-                                                                       reaction product of 2 moles of                                                                         red                              sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,5-diaminonaphthalene                   221    2 moles of 2-bromoaniline-4-                                                                      reaction product of 2 moles of                                                                         red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,5-diaminonaphthalene                   222    2 moles of 2,6-dichloroaniline-                                                                   reaction product of 2 moles of                                                                         red                              4-β-sulfatoethylsulfone                                                                      primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of α,β-bis-(4-aminophenoxy)-                                ethane                                             223    2 moles of 6-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         bluish-tinged                    sulfonyl-2-amino-naphthalene-                                                                     primary condensation product                                                                           redained                         1-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of α,β-bis-(4-aminophenoxy)-                                ethane                                             224    2 moles of 2-naphthylamine-5-                                                                     reaction product of 2 moles of                                                                         bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of α,β-bis-(4-aminophenoxy)-                                ethane                                             225    2 moles of 2-naphthylamine-8-                                                                     reaction product of 2 moles of                                                                         bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of α,β-bis-(4-aminophenoxy)-                                ethane                                             226    2 moles of 2-naphthylamine-6-                                                                     reaction product of 2 moles of                                                                         bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of α,β-bis-(4-aminophenoxy)-                                ethane                                             227    2 moles of 2-chloroaniline-4-                                                                     reaction product of 2 moles of                                                                         red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of α,β-bis-(4-aminophenoxy)-                                ethane                                             228    2 moles of 2-amino-4-β-sulfato-                                                              reaction product of 2 moles of                                                                         red                              ethylsulfonyl-benzoic acid                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of α,β-bis-(4-aminophenoxy)-                                ethane                                             229    2 moles of 5-β-sulfatoethyl-                                                                 reaction product of 2 moles of                                                                         red                              sulfonyl-aniline-2-sulfonic                                                                       primary condensation product obtained                     acid                from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of α,β-bis-(4-aminophenoxy)-                                ethane                                             230    2 moles of aniline-4-β-                                                                      reaction product of 1 mole of                                                                          red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid and                                           1 mole of the primary condensation                                            product obtained from equimolar                                               amounts of cyanuric chloride and 1-                                           amino-8-hydroxynaphthalene-4,6-                                               disulfonic acid with 1 mole of 4,4'-                                          diamino-diphenylamine-3-sulfonic                                              acid                                               231    2 moles of aniline-3-β-                                                                      reaction product of 1 mole of                                                                          yellowish-                       sulfatoethylsulfone primary condensation product                                                                           tinged red                                           from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid and                                           1 mole of the primary condensation                                            product obtained from equimolar                                               amounts of cyanuric chloride and 2-                                           amino-5-naphthol-7-sulfonic acid                                              with 1 mole of 1,4-diamino-2-                                                 methoxybenzene-5-sulfonic acid                     232    2 moles of aniline-4-β-                                                                      reaction product of 1 mole of                                                                          red                              thiosulfatoethylsulfone                                                                           primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid and 1                                         mole of the primary condensation pro-                                         duct obtained from equimolar amounts                                          of cyanuric chloride and 2-amino-8-                                           naphthol-6-sulfonic acid with 1 mole                                          of 1,3-diamino-4-methoxybenzene                    233    2 moles of aniline-4-vinyl-                                                                       reaction product of 1 mole of                                                                          red                              sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxynaphthalene-                                    3,6-disulfonic acid and 1 mole of the                                         primary condensation product obtained from                                    equimolar amounts of cyanuric chloride and                                    2-amino-8-naphthol-6-sulfonic acid with 1                                     mole of 1,3-diamino-4-methoxybenzene               234    2 moles of 2-aminoanisole-4-                                                                      reaction product of 1 mole of                                                                          red                              β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxynaphthalene-                                    3,6-disulfonic acid and 1 mole of the                                         primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxynaphthalene-                                    6-sulfonic acid with 1 mole of 1,4-diamino-                                   benzene-3-sulfonic acid                            235    2 moles of 2-methoxy-5-methyl-                                                                    reaction product of 1 mole of                                                                          bluish-tinged                    aniline-4-β-sulfatoethyl-                                                                    primary condensation product                                                                           redained                         sulfone             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxynaphthalene-                                    3,6-disulfonic acid and 1 mole of the                                         primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxynaphthalene-                                    6-sulfonic acid with 1 mole of 1,4-diamino-                                   benzene-3-sulfonic acid                            236    2 moles of 2,5-dimethoxy-                                                                         reaction product of 1 mole of                                                                          bluish-tinged                    aniline-4-β-sulfatoethyl-                                                                    primary condensation product                                                                           redained                         sulfone             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxynaphthalene-                                    3,6-disulfonic acid and 1 mole of the                                         primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxynaphthalene-                                    6-sulfonic acid with 1 mole of 1,4-diamino-                                   benzene-3-sulfonic acid                            237    2 moles of 8-β-sulfatoethyl-                                                                 reaction product of 1 mole of                                                                          bluish-tinged                    sulfonyl-2-amino-naphthalene-                                                                     primary condensation product                                                                           redained                         6-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxynaphthalene-                                    3,6-disulfonic acid and 1 mole of the                                         primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxynaphthalene-                                    6-sulfonic acid with 1 mole of 1,4-diamino-                                   benzene-3-sulfonic acid                            238    2 moles of 6-β-sulfatoethyl-                                                                 reaction product of 1 mole of                                                                          bluish-tinged                    sulfonyl-2-amino-naphthalene-                                                                     primary condensation product                                                                           redained                         1-sulfonic acid     from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid and 1                                         mole of the primary condensation pro-                                         duct obtained from equimolar amounts                                          of cyanuric chloride and 2-amino-8-                                           hydroxynaphthalene-6-sulfonic acid                                            with 1 mole of 1,4-diaminobenzene-                                            3-sulfonic acid                                    239    2 moles of 2-naphthylamine-6-                                                                     reaction product of 1 mole of                                                                          bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid and 1                                         mole of the primary condensation pro-                                         duct obtained from equimolar amounts                                          of cyanuric chloride and 2-amino-8-                                           hydroxynaphthalene-6-sulfonic acid                                            with 1 mole of 1,4-diaminobenzene-                                            3-sulfonic acid                                    240    2 moles of 2-naphthylamine-8-                                                                     reaction product of 1 mole of                                                                          bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid and 1                                         mole of the primary condensation pro-                                         duct obtained from equimolar amounts                                          of cyanuric chloride and 2-amino-8-                                           hydroxynaphthalene-6-sulfonic acid                                            with 1 mole of 1,4-diaminobenzene-                                            3-sulfonic acid                                    241    2 moles of 2-naphthylamine-5-                                                                     reaction product of 1 mole of                                                                          bluish-tinged                    β-sulfatoethylsulfone                                                                        primary condensation product                                                                           redained                                             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid and 1                                         mole of the primary condensation pro-                                         duct obtained from equimolar amounts                                          of cyanuric chloride and 2-amino-8-                                           hydroxynaphthalene-6-sulfonic acid                                            with 1 mole of 1,4-diaminobenzene-                                            3-sulfonic acid                                    242    2 moles of aniline-4-β-                                                                      reaction product of 1 mole of                                                                          red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4,6-disulfonic acid and 1                                         mole of the primary condensation                                              product obtained from equimolar                                               amounts of cyanuric chloride and 2-                                           amino-8-hydroxynaphthalene-6-                                                 sulfonic acid with 1 mole of 1,3-                                             diaminobenzene-4-sulfonic acid                     243    2 moles of aniline-3-β-                                                                      reaction product of 1 mole of                                                                          red                              sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-4,6-disulfonic acid and 1                                         mole of the primary condensation pro-                                         duct obtained from equimolar amounts                                          of cyanuric chloride and 2-amino-8-                                           hydroxynaphthalene-6-sulfonic acid                                            with 1 mole of 1,3-diaminobenzene-1-                                          sulfonic acid                                      244    2 moles of aniline-4-vinyl-                                                                       reaction product of 1 mole of                                                                          orange                           sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid and 1                                             mole of the primary condensation pro-                                         duct obtained from equimolar amounts                                          of cyanuric chloride and 2-amino-5-                                           naphthol-7-sulfonic acid with 1 mole                                          of 1,4-diaminobenzene-3-sulfonic acid              245    2 moles of aniline-4-β-thio-                                                                 reaction product of 1 mole of                                                                          orange                           sulfatoethylsulfone primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid and 1                                             mole of the primary condensation pro-                                         duct obtained from equimolar amounts                                          of cyanuric chloride and 2-amino-5-                                           naphthol-7-sulfonic acid with 1 mole                                          of 1,4-diaminobenzene-3-sulfonic acid              246    2 moles of 2-aminoanisole-4-                                                                      reaction product of 1 mole of                                                                          orange                           β-sulfatoethylsulfone                                                                        primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 2-amino-8-hydroxy-                                               naphthalene-6-sulfonic acid and 1                                             mole of the primary condensation pro-                                         duct obtained from equimolar amounts                                          of cyanuric chloride and 2-amino-5-                                           naphthol-7-sulfonic acid with 1 mole                                          of 1,4-diaminobenzene-3-sulfonic acid              247    2 moles of aniline-3-vinyl-                                                                       reaction product of 2 moles of                                                                         red                              sulfone             primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 4,4'-diaminoazobenzene                   248    2 moles of 2-aminoanisole-4-                                                                      reaction product of 2 moles of                                                                         claret                           β-thiosulfatoethylsulfone                                                                    primary condensation product obtained                                         from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 4,4'-diaminoazobenzene                   249    2 moles of 2,5-dimethoxy-                                                                         reaction product of 2 moles of                                                                         red                              aniline-4-β-sulfatoethyl-                                                                    primary condensation product obtained                     sulfone             from equimolar amounts of cyanuric                                            chloride and 2-methylamino-8-naphthol-                                        6-sulfonic acid with 1 mole of 4,4'-                                          diaminodiphenylmethane                             250    2 moles of 2-methoxy-5-methyl-                                                                    reaction product of 2 moles of                                                                         claret                           aniline-4-β-sulfatoethyl-                                                                    primary condensation product obtained                     sulfone             from equimolar amounts of cyanuric                                            chloride and 1-amino-8-hydroxy-                                               naphthalene-3,6-disulfonic acid with                                          1 mole of 1,2-bis-(4'-aminophenyl)-                                           ethane                                             __________________________________________________________________________

EXAMPLE 251

18.5 parts by weight of cyanuric chloride are dissolved in 60 parts byvolume of acetone, with warming, and the solution is then poured into500 parts by volume of water at 15°-20° C. A neutral solution of 31.9parts by weight of 1-amino-8-naphthol-3,6-disulfonic acid and 8.5 partsby volume of aqueous 33% sodium hydroxide solution in 150 parts byvolume of water is then added immediately and the resulting mixture isstirred for some time. A neutral solution of 18.5 parts by weight of4,4'-diaminostilbene-2,2'-disulfonic acid and 9 parts by volume ofaqueous 33% sodium hydroxide solution in 250 parts by volume of waterand, immediately thereafter, 30 parts by weight of crystalline sodiumacetate are added and the resulting mixture is stirred for several hoursat 20°-30° C. The suspension of the coupling component which is thusobtained is combined with the following diazonium salt solution: 29.7parts by weight of 4-β-sulfatoethylsulfonyl-2-aminophenol are suspendedin 140 parts by volume of water and 60 parts by weight of ice anddissolved to give a neutral solution by adding 7.6 parts by weight ofsodium carbonate. 20.5 parts by volume of aqueous 5 N sodium nitritesolution are added and the solution thus obtained is added dropwise to amixture of 25 parts by volume of aqueous 31% hydrochloric acid and 150parts by weight of ice. The pH value is adjusted to 5.5-6.5 by adding 13parts by weight of sodium bicarbonate in portions, and the suspension ofthe coupling component described initially is then added. The couplingreaction is carried out for several hours at 22°-24° C., the pH valuebeing kept at 6.0 by adding a total of 19.5 parts by weight of sodiumbicarbonate in portions. After the formation of the dyestuff has ended,the mixture is warmed to about 80° C. and the dyestuff solution isclarified. The solution is allowed to cool to 50° C. and 30 parts byweight of crystalline sodium acetate and 24.7 parts by weight ofcrystalline copper sulfate are added and the mixture is stirred for onehour at 50°-55° C. The dyestuff is precipitated by adding 25%, based onthe volume, of potassium chloride, filtered off, dried in vacuo at 60°C. and ground. This gives a brown-black dyestuff powder which givesreddish-tinged violet dyeings and prints of considerable depth of shadeon cotton when the processes customary for reactive dyestuffs are used.The dyestuff has the following constitution: ##STR106##

EXAMPLE 252

If the corresponding amount of 5-β-sulfatoethylsulfonyl-2-aminophenol isemployed in place of the 4-β-sulfatoethylsulfonyl-2-aminophenol inExample 251 and in other respects the procedure is as indicated inExample 251, this gives a dark brown dyestuff powder with which deepviolet dyeings with very good general fastness properties are obtainedon cellulose materials. In the form of the free acid, the dyestuff hasthe following constitution: ##STR107##

EXAMPLE 253

The reaction product of 18.5 parts by weight of4,4'-diaminostilbene-2,2'-disulfonic acid with the primary condensationproduct of 31.9 parts by weight of1-amino-8-hydroxynaphthalene-3,6-disulfonic acid and 18.5 parts byweight of cyanuric chloride is prepared in the manner described inExample 251. The suspension of this coupling component is combined withthe following diazonium salt solution:

25.1 parts by weight of 2-aminonaphthalene-8-β-hydroxyethylsulfone areintroduced into 66 parts by volume of 20% strength oleum in the courseof about 20 minutes and the mixture is then warmed at 65°-70° C. for 4hours. The reaction mixture is then cooled to 25°-30° C. and is allowedto run into a mixture of 250 parts by weight of ice and 100 parts byvolume of water. The diazotization is then carried out at 0°-5° C. with20 parts by volume of aqueous 5 N sodium nitrite solution, the reactionmixture is stirred for a further one hour at this temperature and then alittle excess nitrous acid is destroyed by means of amidosulfonic acid.The pH of the diazonium salt solution is adjusted to 5.0-5.5 by adding120 parts by weight of calcium carbonate and the solution is added tothe abovementioned suspension of the coupling component.

After the diazonium salt solution has been added, the mixture is stirredfor 16 hours at room temperature, the pH value being kept at 5.5-6.0 byadding about 10.1 parts by weight of calcium carbonate in portions. Themixture is then warmed to 60°-70° C. and the gypsum is filtered off. Thelatter is washed with hot water, and 30 parts by weight of crystallinesodium acetate and 24.7 parts by weight of crystalline copper sulfateare then added to the filtrate and a mixture of 22.7 parts by weight of30% strength hydrogen peroxide and 100 parts by volume of water is addeddropwise at 32°-38° C. in the course of 30 minutes. After 3 hours, thedyestuff solution is clarified and the dyestuff is precipitated byadding potassium chloride, filtered off and dried in vacuo at 60° C.This gives a dark blue powder which gives reddish-tinged blue prints anddyeings on cotton fabric. In the form of the free acid, the dyestuff hasthe following constitution: ##STR108##

EXAMPLE 253a

The non-metallized dyestuff is prepared as described in Example 251.After clarifying, 30 parts by weight of crystalline sodium acetate and29.5 parts by weight of crystalline cobalt sulfate are added to thefiltrate and the mixture is then warmed at 60°-65° C. for 2 hours. Thedyestuff solution is clarified and then evaporated to dryness in vacuo.This gives a dark dyestuff powder with which opaque violet prints can beproduced on cotton in the presence of acid-binding agents. In the formof the free acid, the dyestuff has the following constitution:##STR109##

EXAMPLE 254

The non-metallized dyestuff is prepared as described in Example 251.After clarifying, the filtrate is warmed to 50°-55° C. and, at thistemperature, 32 parts by weight of crystalline sodium acetate and 25parts by weight of chromium-potassium sulfate are added. The temperatureis then raised to the boiling point and the mixture is boiled underreflux for 5 hours. Thereafter, the dyestuff solution is clarified andthen evaporated to dryness in vacuo at 60° C. This gives a grey-blackdyestuff powder with which reddish-tinged grey prints are obtained oncotton fabric in the presence of acid-binding agents. In the form of thefree acid, the dyestuff has the following constitution: ##STR110##

EXAMPLE 255

32.5 parts by weight of2-methoxy-5-methylaniline-4-β-sulfatoethylsulfone are suspended in 150parts by volume of water and 50 parts by weight of ice and dissolved byadding about 6.3 parts by weight of calcined sodium carbonate, the pHvalue being between 6.0 and 6.5. 20.3 parts by volume of aqueous 5 Nsodium nitrite solution and 1.5 parts by weight of kieselguhr are addedand the solution is clarified. The filtrate runs at 0°-5° C. into amixture of 150 parts by weight of ice and 28.2 parts by weight ofaqueous 31% hydrochloric acid. After stirring for one hour at 0°-5° C.,a little excess nitrous acid is destroyed with amidosulfonic acid andthe pH of the resulting diazonium salt solution is then adjusted to 6 byintroducing about 4 parts by weight of sodium bicarbonate. This solutionis combined with the coupling solution described in Example 251. Thecoupling reaction is carried out at 18°-20° C. for several hours, the pHvalue being kept at 5.3-6.1 by adding sodium bicarbonate in portions.When the coupling has ended, a solution of 34.6 parts by weight ofcrystalline copper sulfate, 48.3 parts by weight of crystalline sodiumacetate and 31.8 parts by weight of glacial acetic acid in 147.5 partsby volume of water is added and the resulting mixture is then boiledunder reflux for 18 hours. After cooling, the dyestuff solution isclarified and the dyestuff is then precipitated by adding potassiumchloride, filtered off and dried in vacuo at 60° C. This gives ablue-black powder which in the presence of acid-binding agents dyescellulose materials in reddish-tinged blue shades. In the form of thefree acid, the dyestuff has the following constitution: ##STR111##

The heavy metal complex dyestuffs listed in the table which follows canbe obtained in a manner similar to that described in Examples 251 to255. In the "diazo component" column, the said components are indicatedin the form in which they are present after metallization, that is tosay in some cases with a hydroxyl group formed from a methoxy group bydemethylating metallization or with a hydroxy group introduced byoxidative coppering.

                                      TABLE 2                                     __________________________________________________________________________                                                 Complex-                         Example                                      forming  Color shade             No.   Diazo component   Coupling component   metal    on                      __________________________________________________________________________                                                          cotton                  256   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of the                                                                 chromium bluish-tinged                 5-β-sulfatoethylsulfone                                                                    primary condensation product  grey                                            obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         257   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of the                                                                 cobalt   violet-tinged                 5-β-sulfatoethylsulfone                                                                    primary condensation product  grey                                            obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'disulfonic acid                          258   2 moles of 6-bromo-2-amino-                                                                     reaction product of 2 moles of the                                                                 copper   violet                        phenol-4-β-sulfatoethyl-                                                                   primary condensation product                                sulfone           obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         259   2 moles of 6-bromo-2-amino-                                                                     reaction product of 2 moles of the                                                                 chromium reddish-tinged                phenol-4-β-sulfatoethyl-                                                                   primary condensation product  grey                          sulfone           obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         260   2 moles of 6-bromo-2-amino-                                                                     reaction product of 2 moles of the                                                                 cobalt   opaque violet                 phenol-4-β-sulfatoethyl-                                                                   primary condensation product                                sulfone           obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         261   2 moles of b-nitro-2-amino                                                                      reaction product of 2 moles of the                                                                 copper   violet                        phenol-4-β-sulfatoethyl-                                                                   primary condensation product                                sulfone           obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         262   2 moles of 6-nitro-2-amino-                                                                     reaction product of 2 moles of the                                                                 chromium grey                          phenol-4-β-sulfatoethyl-                                                                   primary condensation product                                sulfone           obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         263   2 moles of 6-nitro-2-amino-                                                                     reaction product of 2 moles of the                                                                 cobalt   grey                          phenol-4-β-sulfatoethyl-                                                                   primary condensation product                                sulfone           obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         264   2 moles of 4-methyl-2-amino-                                                                    reaction product of 2 moles of the                                                                 chromium bluish-tinged                 phenol-5-β-sulfatoethyl-                                                                   primary condensation product  grey                          sulfone           obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         265   2 moles of 4-methyl-2-amino-                                                                    reaction product of 2 moles of the                                                                 cobalt   violet-tinged                 phenol-5-β-sulfatoethyl-                                                                   primary condensation product  grey                          sulfone           obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         266   2 moles of 4-methoxy-2-amino-                                                                   reaction product of 2 moles of the                                                                 copper   reddish-tinged                phenol-5-β-sulfatoethyl-                                                                   primary condensation product  blue                          sulfone           obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         267   2 moles of 4-β-sulfatoethyl-                                                               reaction product of 2 moles of the                                                                 copper   violet                        sulfonyl-2-aminophenol-6-                                                                       primary condensation product                                sulfonic acid     obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         268   2 moles of 4-β-sulfatoethyl-                                                               reaction product of 2 moles of the                                                                 chromium reddish-tinged                sulfonyl-2-aminophenol-6-                                                                       primary condensation product  grey                          sulfonic acid     obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         269   2 moles of 4-β-sulfatoethyl-                                                               reaction product of 2 moles of the                                                                 cobalt   opaque violet                 sulfonyl-2-aminophenol-6-                                                                       primary condensation product                                sulfonic acid     obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         270   2 moles of 8-β-sulfatoethyl-                                                               reaction product of 2 moles of the                                                                 copper   reddish-tinged                sulfonyl-1-hydroxy-2-amino-                                                                     primary condensation product  blue                          naphthalene-6-sulfonic acid                                                                     obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              hydroxynaphthalene-3,6-disulfonic                                             acid with 1 mole of 4,4'-diamino-                                             stilbene-2,2'-disulfonic acid                         271   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of the                                                                 copper   violet                        4-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-hydroxynaphthalene-3,6-disul-                                               fonic acid with 1 mole of 3,3'-                                               dimethyl-benzidine-6,6'-disulfonic                                            acid                                                  272   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     chromium reddish-tinged                4-β-sulfatoethylsulfone                                                                    the primary condensation product                                                                            grey                                            obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-hydroxynaphthalene-3,6-disul-                                               fonic acid with 1 mole of 3,3'-                                               dimethyl-benzidine-6,6'-disulfonic                                            acid                                                  273   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     cobalt   opaque violet                 4-β-sulfatoethylfulfone                                                                    the primary condensation product                                              obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-hydroxynaphthalene-3,6-disul-                                               fonic acid with 1 mole of 3,3'-                                               dimethyl-benzidine-6,6'-disulfonic                                            acid                                                  274   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     copper   violet                        5-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-hydroxynaphthalene-3,6-disul-                                               fonic acid with 1 mole of 3,3'-                                               dimethyl-benzidine-6,6'-disulfonic                                            acid                                                  275   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     chromium bluish-tinged                 5-β-sulfatoethylsulfone                                                                    the primary condensation product                                                                            grey                                            obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-hydroxynaphthalene-3,6-disul-                                               fonic acid with 1 mole of 3,3'-                                               dimethyl-benzidine-6,6'-disulfonic                                            acid                                                  276   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     cobalt   violet-tinged                 5-β-sulfatoethylsulfone                                                                    the primary condensation product                                                                            grey                                            obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-hydroxynaphthalene-3,6-disul-                                               fonic acid with 1 mole of 3,3'-                                               dimethyl-benzidine-6,6'-disulfonic                                            acid                                                  277   2 moles of 6-chloro-2-amino-                                                                    reaction product of 2 moles of                                                                     copper   violet                        phenol-4-β-sulfatoethyl-                                                                   the primary condensation product                            sulfone           obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-hydroxynaphthalene-3,6-disul-                                               fonic acid with 1 mole of 3,3'-                                               dimethyl-benzidine-6,6'-disulfonic                                            acid                                                  278   2 moles of 6-chloro-2-amino-                                                                    reaction product of 2 moles of                                                                     chromium reddish-tinged                phenol-4-β-sulfatoethyl-                                                                   the primary condensation product                                                                            grey                          sulfone           obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-hydroxynaphthalene-3,6-disul-                                               fonic acid with 1 mole of 3,3'-                                               dimethyl-benzidine-6,6'-disulfonic                                            acid                                                  279   2 moles of 6-chloro-2-amino-                                                                    reaction product of 2 moles of                                                                     cobalt   opaque violet                 phenol-4-β-sulfatoethyl-                                                                   the primary condensation product                            sulfone           obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-hydroxynaphthalene-3,6-disul-                                               fonic acid with 1 mole of 3,3'-                                               dimethyl-benzidine-6,6'-disulfonic                                            acid                                                  280   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     copper   violet                        4-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid with                                             1 mole of 1,6-diaminohexane                           281   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     chromium reddish-tinged                4-β-sulfatoethylsulfone                                                                    the primary condensation product                                                                            grey                                            obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid with                                             1 mole of 1,6-diaminohexane                           282   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     cobalt   violet                        4-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid with                                             1 mole of 1,6-diaminohexane                           283   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     copper   violet                        5-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid with                                             1 mole of 1,6-diaminohexane                           284   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     chromium bluish-tinged                 5-β-sulfatoethylsulfone                                                                    the primary condensation product                                                                            grey                                            obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid with                                             1 mole of 1,6-diaminohexane                           285   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     cobalt   violet-tinged                 5-β-sulfatoethylsulfone                                                                    the primary condensation product                                                                            grey                                            obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid with                                             1 mole of 1,6-diaminohexane                           286   2 moles of 8-β-sulfato-                                                                    reaction product of 2 moles of                                                                     copper   reddish-tinged                ethylsulfonyl-1-hydroxy-2-                                                                      the primary condensation product                                                                            blue                          amino-naphthalene-6-                                                                            obtained from equimolar amounts of                          sulfonic acid     cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid with                                             1 mole of 1,6-diaminohexane                           287   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     copper   violet                        4-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid with                                           1 mole of di-(3-amino-4-sulfophenyl)-                                         sulfone                                               288   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     chromium reddish-tinged                4-β-sulfatoethylsulfone                                                                    the primary condensation product                                                                            grey                                            obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid                                                with 1 mole of di-(3-amino-4-sulfo-                                           phenyl)-sulfone                                       289   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  cobalt   opaque violet                 4-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid                                                with 1 mole of the primary con-                                               densation product obtained from                                               equimolar amounts of cyanuric                                                 chloride and 6-amino-2-naphthol-                                              4-sulfonic acid with 1 mole of                                                1,4-diaminobenzene-2-sulfonic                                                 acid                                                  290   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  copper   violet                        5-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid                                                with 1 mole of the primary con-                                               densation product obtained from                                               equimolar amounts of cyanuric                                                 chloride and 6-amino-2-naphthol-                                              4-sulfonic acid with 1 mole of                                                1,4-diaminobenzene-2-sulfonic                                                 acid                                                  291   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  chromium bluish-tinged                 5-β-sulfatoethylsulfone                                                                    primary condensation product  grey                                            obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid                                                with 1 mole of the primary con-                                               densation product obtained from                                               equimolar amounts of cyanuric                                                 chloride and 6-amino-2-naphthol-                                              4-sulfonic acid with 1 mole of                                                1,4-diaminobenzene-2-sulfonic                                                 acid                                                  292   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  cobalt   violet-tinged                 5-β-sulfatoethylsulfone                                                                    primary condensation product  grey                                            obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid                                                with 1 mole of the primary con-                                               densation product obtained from                                               equimolar amounts of cyanuric                                                 chloride and 6-amino-2-naphthol-                                              4-sulfonic acid with 1 mole of                                                1,4-diaminobenzene-2-sulfonic                                                 acid                                                  293   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  copper   violet                        4-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid,                                               1 mole of the primary conden-                                                 sation product obtained from                                                  equimolar amounts of cyanuric                                                 chloride and 2-amino-8-naphthol-                                              6-sulfonic acid with 1 mole of                                                1,3-diaminobenzene-4-sulfonic acid                    294   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  copper   violet                        4-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid,                                               1 mole of the primary conden-                                                 sation product obtained from                                                  equimolar amounts of cyanuric                                                 chloride and 2-amino-5-naphthol-                                              7-sulfonic acid with 1 mole of                                                1,4-diaminobenzene-2-sulfonic                                                 acid                                                  295   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  copper   violet                        5-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid,                                               1 mole of the primary conden-                                                 sation product obtained from                                                  equimolar amounts of cyanuric                                                 chloride and 2-amino-5-napthol-                                               7-sulfonic acid with 1 mole of                                                1,4-diaminobenzene-2-sulfonic                                                 acid                                                  296   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  chromium violet-brown                  5-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid,                                               1 mole of the primary conden-                                                 sation product obtained from                                                  equimolar amounts of cyanuric                                                 chloride and 2-amino-5-naphthol-                                              7-sulfonic acid with 1 mole of                                                1,4-diaminobenzene-2-sulfonic                                                 acid                                                  297   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  cobalt   brown-violet                  5-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid,                                               1 mole of the primary conden-                                                 sation product obtained from                                                  equimolar amounts of cyanuric                                                 chloride and 2-amino-5-naphthol-                                              7-sulfonic acid with 1 mole of                                                1,4-diaminobenzene-2-sulfonic                                                 acid                                                  298   2 moles of 8-β-sulfatoethyl-                                                               reaction product of 1 mole of the                                                                  copper   reddish-tinged                sulfonyl-2-amino-1-naphthol-                                                                    primary condensation product  blue                          6-sulfonic acid   obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid,                                               1 mole of the primary conden-                                                 sation product obtained from                                                  equimolar amounts of cyanuric                                                 chloride and 2-amino-5-naphthol-                                              7-sulfonic acid with 1 mole of                                                1,4-diaminobenzene-2-sulfonic                                                 acid                                                  299   2 moles of 6-bromo-2-amino-                                                                     reaction product of 1 mole of the                                                                  copper   violet                        phenol-4-β-sulfatoethyl-                                                                   primary condensation product                                sulfone           obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid,                                               1 mole of the primary conden-                                                 sation product obtained from                                                  equimolar amounts of cyanuric                                                 chloride and 2-amino-5-naphthol-                                              7-sulfonic acid with 1 mole of                                                1,4-diaminobenzene-2-sulfonic                                                 acid                                                  300   2 moles of 6-nitro-2-amino-                                                                     reaction product of 1 mole of the                                                                  cobalt   brown-black                   phenol-4-β-sulfatoethyl-                                                                   primary condensation product                                sulfone           obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid,                                               1 mole of the primary conden-                                                 sation product obtained from                                                  equimolar amounts of cyanuric                                                 chloride and 2-amino-5-naphthol-                                              7-sulfonic acid with 1 mole of                                                1,4-diaminobenzene-2-sulfonic                                                 acid                                                  301   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  copper   violet                        4-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             8-naphthol-3,6-disulfonic acid,                                               1 mole of the primary condensation                                            product obtained from equimolar                                               amounts of cyanuric chloride and                                              2-amino-8-naphthol-6-sulfonic                                                 acid with 1 mole of 1,3-diamino-                                              benzene-4-sulfonic acid                               302   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  chromium grey-violet                   4-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid, 1                                               mole of the primary condensation                                              product obtained from equimolar                                               amounts of cyanuric chloride and                                              2-amino-8-naphthol-6-sulfonic                                                 acid with 1 mole of 1,3-diamino-                                              benzene-4-sulfonic acid                               303   2 moles of 2-aminophenol-                                                                       reaction production of 1 mole of                                                                   cobalt   brown-violet                  4-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid, 1                                               mole of the primary condensation                                              product obtained from equimolar                                               amounts of cyanuric chloride and                                              2-amino-8-naphthol-6-sulfonic                                                 acid with 1 mole of 1,3-diamino-                                              benzene-4-sulfonic acid                               304   2 moles of 2-aminophenol-                                                                       reaction production of 1 mole of                                                                   copper   violet                        5-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid, 1                                               mole of the primary condensation                                              product obtained from equimolar                                               amounts of cyanuric chloride and                                              2-amino-8-naphthol-6-sulfonic                                                 acid with 1 mole of 1,3-diamino-                                              benzene-4-sulfonic acid                               305   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  chromium grey-violet                   5-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid, 1                                               mole of the primary condensation                                              product obtained from equimolar                                               amounts of cyanuric chloride and                                              2-amino-8-naphthol-6-sulfonic                                                 acid with 1 mole of 1,3-diamino-                                              benzene-4-sulfonic acid                               306   2 moles of 2-aminophenol-                                                                       reaction product of 1 mole of the                                                                  cobalt   opaque violet                 5-β-sulfatoethylsulfone                                                                    primary condensation product                                                  obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid, 1                                               mole of the primary condensation                                              product obtained from equimolar                                               amounts of cyanuric chloride and                                              2-amino-8-naphthol-6-sulfonic                                                 acid with 1 mole of 1,3-diamino-                                              benzene-4-sulfonic acid                               307   2 moles of 4-methyl-2-                                                                          reaction product of 1 mole of the                                                                  copper   violet                        aminophenol-5-β-sulfato-                                                                   primary condensation product                                ethylsulfone      obtained from equimolar amounts of                                            cyanuric chloride and 1-amino-8-                                              naphthol-3,6-disulfonic acid, 1                                               mole of the primary condensation                                              product obtained from equimolar                                               amounts of cyanuric chloride and                                              2-amino-8-naphthol-6-sulfonic                                                 acid with 1 mole of 1,3-diamino-                                              benzene-4-sulfonic acid                               308   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     copper   claret                        4-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts                                               of cyanuric chloride and 2-amino-                                             5-naphthol-7-sulfonic acid with 1                                             mole of 1,4-diaminobutane                             309   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     cobalt   brown                         4-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts                                               of cyanuric chloride and 2-amino-                                             5-naphthol-7-sulfonic acid with                                               1 mole of 1,4-diaminobutane                           310   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     chromium black                         4-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts                                               of cyanuric chloride and 2-amino-                                             5-naphthol-7-sulfonic acid with                                               1 mole of 1,4-diaminobutane                           311   2 moles of 6-nitro-2-amino-                                                                     reaction product of 2 moles of                                                                     chromium black                         phenol-4-β-sulfatoethyl-                                                                   the primary condensation product                            sulfone           obtained from equimolar amounts                                               of cyanuric chloride and 2-amino-                                             5-naphthol-7-sulfonic acid with                                               1 mole of 1,4-diaminobutane                           312   2 moles of 6-nitro-2-amino-                                                                     reaction product of 2 moles of                                                                     copper   red-violet                    phenol-4-β-sulfatoethyl-                                                                   the primary condensation product                            sulfone           obtained from equimolar amounts                                               of cyanuric chloride and 2-amino-                                             5-naphthol-7-sulfonic acid with                                               1 mole of 1,4-diaminobutane                           313   2 moles of 2-amino-phenol-                                                                      reaction product of 2 moles of                                                                     chromium black-brown                   4-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts                                               of cyanuric chloride and 2-amino-                                             5-naphthol-7-sulfonic acid with                                               1 mole of 1,3-diaminobenzene-4-                                               sulfonic acid                                         314   2 moles of 2-amino-phenol-                                                                      reaction product of 2 moles of                                                                     copper   violet                        4-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts                                               of cyanuric chloride and 2-amino-                                             5-naphthol-7-sulfonic acid with                                               1 mole of 1,3-diaminobenzene-4-                                               sulfonic acid                                         315   2 moles of 2-amino-phenol-                                                                      reaction product of 2 moles of                                                                     cobalt   brown                         4-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts                                               of cyanuric chloride and 2-amino-                                             5-naphthol-7-sulfonic acid with                                               1 mole of 1,3-diaminobenzene-4-                                               sulfonic acid                                         316   2 moles of 6-nitro-2-amino-                                                                     reaction product of 2 moles of                                                                     chromium black                         phenol-4-β-sulfatoethyl-                                                                   the primary condensation product                            sulfone           obtained from equimolar amounts                                               of cyanuric chloride and 2-amino-                                             5-naphthol-7-sulfonic acid with                                               1 mole of 1,3-diaminobenzene-4-                                               sulfonic acid                                         317   2 moles of 6-nitro-2-amino-                                                                     reaction product of 2 moles of                                                                     copper   red-violet                    phenol-4-β-sulfatoethyl-                                                                   the primary condensation product                            sulfone           obtained from equimolar amounts                                               of cyanuric chloride and 2-amino-                                             5-naphthol-7-sulfonic acid with                                               1 mole of 1,3-diaminobenzene-4-                                               sulfonic acid                                         318   2 moles of 2-aminophenol-                                                                       reaction product of 2 moles of                                                                     copper   red-violet                    4-β-sulfatoethylsulfone                                                                    the primary condensation product                                              obtained from equimolar amounts                                               of cyanuric chloride and 1-amino-                                             5-naphthol-7-sulfonic acid with                                               1 mole of 1,5-diaminonaphthalene-                                             3-sulfonic acid                                       __________________________________________________________________________

What is claimed is:
 1. A water soluble dyestuff which in the form of thefree acid has the formula (1) ##STR112## in which K₁ and K₂ areidentical or different to each other and have in the form of the freeacid, the formula ##STR113## in which R is hydrogen or alkyl and p is 1or 2, K₁ and K₂ being bonded via the amino groups to the s-triazineradicals and bonded by the azo groups in ortho-position to their hydroxygroups, D is a benzene nucleus or naphthalene nucleus, R₁ is inortho-position to the azo group and is hydrogen, halogen, lower alkyl,lower alkoxy, hydroxy, carboxy or sulfo and R₂ is hydrogen, halogen,lower alkyl, lower alkoxy, nitro or sulfo, R₁ and R₂ being identical ordifferent from one another; X is β-thiosulfatoethyl, β-chloroethyl,β-sulfatoethyl or vinyl, A is an aliphatic radical of 2-10 C atoms or analiphatic radical of, in total, 2-6 C atoms, which may be interrupted bya hetero-atom and/or a cycloaliphatic radical, or is a cycloaliphaticradical or is a benzene nucleus or a naphthalene nucleus, these nucleibeing unsubstituted or substituted by substituents selected from thegroup consisting of lower alkyl, lower alkoxy, chlorine, sulfo, carboxyand lower alkanoylamino, or is ##STR114## in each of which the benzenenuclei may be substituted by substituents selected from the groupconsisting of lower alkyl, lower alkoxy, sulfo, carboxy and chlorine,and D₁ is a direct covalent bond or a bridge member and E is --O--,--S--, --NH-- or --SO₂ --, Y is chlorine, fluorine, bromine, sulfo or agroup of the formula --S--R'-- or --O--R", in which R' is a substituentselected from the group consisting of lower alkyl, substituted loweralkyl, phenyl, naphthyl, substituted phenyl, substituted naphthyl or2-benzthiazolyl and R" is hydrogen or has the meaning of R' with theexception of 2-benzthiazolyl, or Y is an amino group of the formula--NR₃ R₄, in which R₃ is hydrogen, an optionally substituted loweraliphatic radical, an optionally substituted araliphatic radical or acycloaliphatic radical and R₄ is hydrogen, an optionally substitutedlower aliphatic radical or an optionally substituted aromatic radical oran optionally substituted araliphatic radical or is hydroxy or loweralkoxy or an optionally substituted amino group, or R₃ and R₄ togetherwith the nitrogen atom form a ring containing lower alkylene andoptionally a hetero-atom, and a copper, chromium or cobalt complexdyestuff of the compounds of formula (1) wherein one or both of the R₁ sare hydroxy.
 2. A dyestuff according to claim 1 in which D, R₁, R₂, K₁,K₂, A and X are as defined in claim 1 and Y is chlorine, bromine,fluorine, sulfo, amino, methylamino, dimethylamino,β-hydroxyethyl-amino, β-methoxyethyl-amino, β-sulfatoethylamino,β-sulfoethyl-amino, N-methyl-N-β-sulfoethyl-amino, carboxymethyl-amino,N-β-carboxyethyl-amino, N-(carboxyphenyl)-amino, N-(sulfophenyl)-amino,N-(disulfophenyl)-amino, N-(sulfonaphthyl(1))-amino, N-methyl-anilino,morpholino, iso-propoxy, phenoxy or β-hydroxyethyl-thioether.
 3. Adyestuff according to claim 1 with D, R₁, R₂, K₁, K₂, A and X as definedin claim 1 and Y is chlorine.
 4. A dyestuff according to claim 1, 2 or3, with Y, R₁, R₂, K₁, K₂, A and X as defined in claim 1, 2 or 3 and Dis a benzene nucleus.
 5. A dyestuff according to claim 1, 2 or 3, withY, K₁, K₂, A and X as defined in claim 1, 2 or 3 and D is thenaphthalene nucleus bonded in 2-position to the azo, R₁ is hydrogen andR₂ is sulfo in the 6-position of the naphthalene nucleus, or R₁ is sulfoand R₂ is hydrogen.
 6. A dyestuff according to claim 4, in which --SO₂--X is in the meta-position or para-position to the azo group.
 7. Adyestuff according to claim 5, with the meanings defined in claim 5, inwhich D is a naphthalene nucleus bonded in the 2-position to the azogroup and --SO₂ --X is bonded in the 6-position or 8-position.
 8. Adyestuff according to claim 1, wherein X is vinyl or β-sulfatoethyl. 9.A dyestuff according to claim 1, in which A is alkylene of 2 to 6 Catoms, optionally being interrupted by 1 or 2 members selected from thegroup consisting of --NH--, --O--, --N(CH₃)--, --S-- and cyclohexylene,or is cyclohexylene unsubstituted or substituted by 1-3 methyl, or is abenzene nucleus or a naphthalene nucleus unsubstituted or substituted bysubstituents selected from the group consisting of lower alkyl, loweralkoxy, chlorine, sulfo, carboxy and lower alkanoylamino, or is##STR115## in which each of the benzene nuclei can be substituted by 1or 2 substituents selected from the group consisting of lower alkyl,lower alkoxy, sulfo, carboxy and chlorine and D₁ is a direct covalentbond or --CH₂ --, --CH₂ --CH₂ --, --O--CH₂ --CH₂ --O--, --CH═CH--,--NH--, --O--, --S--, --SO₂ --, --N═N--, --NH--CO--NH--, --CO--NH--,--NH--CO--, ##STR116## and E is --O--, --S--, --NH-- or --SO₂ --.
 10. Adyestuff as claimed in claim 1, wherein K₁ and K₂ each is the bivalentradical of 1-amino-naphthol-(8)-3,6-disulfonic acid.
 11. A dyestuffaccording to claim 1 in which D, R₁, R₂, K₁ and K₂ are as defined inclaim 1 and Y is chlorine, X is β-sulfatoethyl and A is ##STR117##
 12. Adyestuff according to claim 1 or 9, with D, R₁, R₂ and A as defined inclaim 1 or 9, and X is β-sulfatoethyl, Y is chlorine, K₁ is ##STR118##and K₂ is ##STR119##
 13. A dyestuff according to claim 1 in which D is abenzene nucleus, R₁ and R₂ are each hydrogen, X is β-sulfatoethyl, thisβ-sulfatoethylsulfonyl being in the p-position to the azo group, Y ischlorine, A is ##STR120## K₁ is ##STR121## and K₂ is ##STR122##
 14. Acopper, chromium or cobalt complex dyestuff according to claim
 1. 15. Adyestuff of the formula ##STR123##
 16. A dyestuff of the formula##STR124##